Stereospecific synthesis of trans-2,3-diaryl substituted 1-aminocyclopropanecarboxylic acid derivatives

Synthetic Communications

Volumn 33, Issue 16, 2003, Pages 2873-2884

  Su, Guifa ^a,b,c,d   Mu, Hongtao ^b   Za, Danming ^b   Zeng, Longmei ^a   Cativiela, Carlos ^c   Hammer, Robert P ^d   Yu, Kaibei ^e  

^a SUN YAT SEN UNIVERSITY   (China)

^b GUANGXI NORMAL UNIVERSITY   (China)

^c CSIC   (Spain)

^d LOUISIANA STATE UNIVERSITY   (United States)

^e INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

Author keywords

1,3 Dipolar cycloaddition; Oxazolones; Phenyldiazomethane; Stereospecific syntheses; Trans 2,3 Diaryl 1 amino cyclopropanecarboxylic acid

Indexed keywords

1 AMINOCYCLOPROPANECARBOXYLIC ACID DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; CYCLOPROPANE DERIVATIVE; OXAZOLONE; PHENYLDIAZOMETHANE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0043131887     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120022177     Document Type: Article

References (47)

1. Burroughs, L.F. 1-Aminocyclopropane-1-carboxylic acid: a new amino acid in perry pears and cider apples. Nature 1957, 179, 360-361.
2. Adams, D.O.; Yang, S.F. Ethylene biosynthesis: Identification of 1-aminocyclopropane-1-carboxylic acid as an intermediate in the conversion of methionine to ethylene. Proc. Natl. Acad. Sci. USA 1979, 76 (1), 170-174.
3. For recent reviews on ACCs, see: (a) Salaun, J. Cyclopropane derivatives and their diverse biological activities. Top. Curr. Chem. 2000, 207, 1-67; (b) Cativiela, C.; Diaz-de-Viellgas, M.D. Stereoselective synthesis of quaternary α-amino acids. Part 2: cyclic compounds. Tetrahedron: Asymmetry 2000, 11 (3), 645-732; (c) Salaun, J.; Baird, M.S. Biologically active cyclopropanes and cyclopropenes. Curr. Med. Chem. 1995, 2 (1), 511-542; (d) Burgess, K.; Ho, K.-K.; Moye-Sherman, D. Asymmetric syntheses of 2,3-methanoamino acids. Synlett 1994, 8, 575-583.
4. For recent reviews on ACCs, see: (a) Salaun, J. Cyclopropane derivatives and their diverse biological activities. Top. Curr. Chem. 2000, 207, 1-67; (b) Cativiela, C.; Diaz-de-Viellgas, M.D. Stereoselective synthesis of quaternary α-amino acids. Part 2: cyclic compounds. Tetrahedron: Asymmetry 2000, 11 (3), 645-732; (c) Salaun, J.; Baird, M.S. Biologically active cyclopropanes and cyclopropenes. Curr. Med. Chem. 1995, 2 (1), 511-542; (d) Burgess, K.; Ho, K.-K.; Moye-Sherman, D. Asymmetric syntheses of 2,3-methanoamino acids. Synlett 1994, 8, 575-583.
5. For recent reviews on ACCs, see: (a) Salaun, J. Cyclopropane derivatives and their diverse biological activities. Top. Curr. Chem. 2000, 207, 1-67; (b) Cativiela, C.; Diaz-de-Viellgas, M.D. Stereoselective synthesis of quaternary α-amino acids. Part 2: cyclic compounds. Tetrahedron: Asymmetry 2000, 11 (3), 645-732; (c) Salaun, J.; Baird, M.S. Biologically active cyclopropanes and cyclopropenes. Curr. Med. Chem. 1995, 2 (1), 511-542; (d) Burgess, K.; Ho, K.-K.; Moye-Sherman, D. Asymmetric syntheses of 2,3-methanoamino acids. Synlett 1994, 8, 575-583.
6. For recent reviews on ACCs, see: (a) Salaun, J. Cyclopropane derivatives and their diverse biological activities. Top. Curr. Chem. 2000, 207, 1-67; (b) Cativiela, C.; Diaz-de-Viellgas, M.D. Stereoselective synthesis of quaternary α-amino acids. Part 2: cyclic compounds. Tetrahedron: Asymmetry 2000, 11 (3), 645-732; (c) Salaun, J.; Baird, M.S. Biologically active cyclopropanes and cyclopropenes. Curr. Med. Chem. 1995, 2 (1), 511-542; (d) Burgess, K.; Ho, K.-K.; Moye-Sherman, D. Asymmetric syntheses of 2,3-methanoamino acids. Synlett 1994, 8, 575-583.
7. 1-conformations of phenylalanine. Chem. Eur. J. 1999, 5 (9), 2730-2739; (c) Jimenez, A.I.; Cativiela, C.; Aubry, A.; Marraud, M. β-Turn preferences induced by 2,3-methanophenylalanine chirality. J. Am. Chem. Soc. 1998, 120 (37), 9452-9459; (d) Moye-Sherman, D.; Jin, S.; Ham, I.; Burgess, K. Conformational preferences of RNase A C-peptide derivatives containing a highly constrained analog of phenylalanine. J. Am. Chem. Soc. 1998, 120 (37), 9435-9443; (e) Lim, D.; Burgess, K. Spirocyclic peptidomimetics featuring 2,3-methanoamino acids. J. Am. Chem. Soc. 1997, 119 (41), 9632-9640; (f) Jimenez, A.I.; Vandersse, R.; Marraud, M.; Aubry, A.; Cativiela, C. Folding types of dipeptides containing the diastereoisomeric cyclopropanic analogs of phenylalanine. Tetra. Lett. 1997, 38 (43), 7559-7562; (g) Burgess, K.; Ke, C.-Y. On the conformational bias of F((2R,3S)-cyclo-M)RFa induced by the cis-2,3-methanomethionine residue. J. Org. Chem. 1996, 61 (24), 8627-8631; (h) Burgess, K.; Ho, K.-K.; Pal, B. Comparison of the effects of (2S,3S)-2,3-methanomethionine, (2R,3R)-2,3-methano-methionine, and (2R,3R)-2,3-methanophenylalanine on the conformations of small peptides. J. Am. Chem. Soc. 1995, 117 (13), 3808-3819; (i) Burgess, K.; Ho, K.-K.; Pettitt, B.M. J. Am. Chem. Soc. Conformational effects of substituting methionine with (2S,3S)-2,3-methanomethionine in Phe-Met-Arg-Phe-NH2. 1995, 117 (1), 54-65; (j) Balaji, V.N.; Ramnarayan, K.; Chan, M.-F.; Rao, S. Conformational studies on model peptides with 1-aminocyclopropane-1-carboxylic acid residues. Pep. Res. 1994, 7 (2), 60-71; (k) Burgess, K.; Ho, K.-K.; Pettitt, B.M. A γ-turn structure induced by 2S,3S-2,3-methanomethionine. J. Am. Chem. Soc. 1994, 116 (2), 799-800; (l) Mapelli, C.; Newton, M.G.; Ringold, C.E.; Stammer, C.H. Cyclopropane amino acid ester dipeptide sweeteners. Int. J. Peptide Protein Res. 1987, 30 (4), 498-510.
8. 1-conformations of phenylalanine. Chem. Eur. J. 1999, 5 (9), 2730-2739; (c) Jimenez, A.I.; Cativiela, C.; Aubry, A.; Marraud, M. β-Turn preferences induced by 2,3-methanophenylalanine chirality. J. Am. Chem. Soc. 1998, 120 (37), 9452-9459; (d) Moye-Sherman, D.; Jin, S.; Ham, I.; Burgess, K. Conformational preferences of RNase A C-peptide derivatives containing a highly constrained analog of phenylalanine. J. Am. Chem. Soc. 1998, 120 (37), 9435-9443; (e) Lim, D.; Burgess, K. Spirocyclic peptidomimetics featuring 2,3-methanoamino acids. J. Am. Chem. Soc. 1997, 119 (41), 9632-9640; (f) Jimenez, A.I.; Vandersse, R.; Marraud, M.; Aubry, A.; Cativiela, C. Folding types of dipeptides containing the diastereoisomeric cyclopropanic analogs of phenylalanine. Tetra. Lett. 1997, 38 (43), 7559-7562; (g) Burgess, K.; Ke, C.-Y. On the conformational bias of F((2R,3S)-cyclo-M)RFa induced by the cis-2,3-methanomethionine residue. J. Org. Chem. 1996, 61 (24), 8627-8631; (h) Burgess, K.; Ho, K.-K.; Pal, B. Comparison of the effects of (2S,3S)-2,3-methanomethionine, (2R,3R)-2,3-methano-methionine, and (2R,3R)-2,3-methanophenylalanine on the conformations of small peptides. J. Am. Chem. Soc. 1995, 117 (13), 3808-3819; (i) Burgess, K.; Ho, K.-K.; Pettitt, B.M. J. Am. Chem. Soc. Conformational effects of substituting methionine with (2S,3S)-2,3-methanomethionine in Phe-Met-Arg-Phe-NH2. 1995, 117 (1), 54-65; (j) Balaji, V.N.; Ramnarayan, K.; Chan, M.-F.; Rao, S. Conformational studies on model peptides with 1-aminocyclopropane-1-carboxylic acid residues. Pep. Res. 1994, 7 (2), 60-71; (k) Burgess, K.; Ho, K.-K.; Pettitt, B.M. A γ-turn structure induced by 2S,3S-2,3-methanomethionine. J. Am. Chem. Soc. 1994, 116 (2), 799-800; (l) Mapelli, C.; Newton, M.G.; Ringold, C.E.; Stammer, C.H. Cyclopropane amino acid ester dipeptide sweeteners. Int. J. Peptide Protein Res. 1987, 30 (4), 498-510.
9. 1-conformations of phenylalanine. Chem. Eur. J. 1999, 5 (9), 2730-2739; (c) Jimenez, A.I.; Cativiela, C.; Aubry, A.; Marraud, M. β-Turn preferences induced by 2,3-methanophenylalanine chirality. J. Am. Chem. Soc. 1998, 120 (37), 9452-9459; (d) Moye-Sherman, D.; Jin, S.; Ham, I.; Burgess, K. Conformational preferences of RNase A C-peptide derivatives containing a highly constrained analog of phenylalanine. J. Am. Chem. Soc. 1998, 120 (37), 9435-9443; (e) Lim, D.; Burgess, K. Spirocyclic peptidomimetics featuring 2,3-methanoamino acids. J. Am. Chem. Soc. 1997, 119 (41), 9632-9640; (f) Jimenez, A.I.; Vandersse, R.; Marraud, M.; Aubry, A.; Cativiela, C. Folding types of dipeptides containing the diastereoisomeric cyclopropanic analogs of phenylalanine. Tetra. Lett. 1997, 38 (43), 7559-7562; (g) Burgess, K.; Ke, C.-Y. On the conformational bias of F((2R,3S)-cyclo-M)RFa induced by the cis-2,3-methanomethionine residue. J. Org. Chem. 1996, 61 (24), 8627-8631; (h) Burgess, K.; Ho, K.-K.; Pal, B. Comparison of the effects of (2S,3S)-2,3-methanomethionine, (2R,3R)-2,3-methano-methionine, and (2R,3R)-2,3-methanophenylalanine on the conformations of small peptides. J. Am. Chem. Soc. 1995, 117 (13), 3808-3819; (i) Burgess, K.; Ho, K.-K.; Pettitt, B.M. J. Am. Chem. Soc. Conformational effects of substituting methionine with (2S,3S)-2,3-methanomethionine in Phe-Met-Arg-Phe-NH2. 1995, 117 (1), 54-65; (j) Balaji, V.N.; Ramnarayan, K.; Chan, M.-F.; Rao, S. Conformational studies on model peptides with 1-aminocyclopropane-1-carboxylic acid residues. Pep. Res. 1994, 7 (2), 60-71; (k) Burgess, K.; Ho, K.-K.; Pettitt, B.M. A γ-turn structure induced by 2S,3S-2,3-methanomethionine. J. Am. Chem. Soc. 1994, 116 (2), 799-800; (l) Mapelli, C.; Newton, M.G.; Ringold, C.E.; Stammer, C.H. Cyclopropane amino acid ester dipeptide sweeteners. Int. J. Peptide Protein Res. 1987, 30 (4), 498-510.
10. 1-conformations of phenylalanine. Chem. Eur. J. 1999, 5 (9), 2730-2739; (c) Jimenez, A.I.; Cativiela, C.; Aubry, A.; Marraud, M. β-Turn preferences induced by 2,3-methanophenylalanine chirality. J. Am. Chem. Soc. 1998, 120 (37), 9452-9459; (d) Moye-Sherman, D.; Jin, S.; Ham, I.; Burgess, K. Conformational preferences of RNase A C-peptide derivatives containing a highly constrained analog of phenylalanine. J. Am. Chem. Soc. 1998, 120 (37), 9435-9443; (e) Lim, D.; Burgess, K. Spirocyclic peptidomimetics featuring 2,3-methanoamino acids. J. Am. Chem. Soc. 1997, 119 (41), 9632-9640; (f) Jimenez, A.I.; Vandersse, R.; Marraud, M.; Aubry, A.; Cativiela, C. Folding types of dipeptides containing the diastereoisomeric cyclopropanic analogs of phenylalanine. Tetra. Lett. 1997, 38 (43), 7559-7562; (g) Burgess, K.; Ke, C.-Y. On the conformational bias of F((2R,3S)-cyclo-M)RFa induced by the cis-2,3-methanomethionine residue. J. Org. Chem. 1996, 61 (24), 8627-8631; (h) Burgess, K.; Ho, K.-K.; Pal, B. Comparison of the effects of (2S,3S)-2,3-methanomethionine, (2R,3R)-2,3-methano-methionine, and (2R,3R)-2,3-methanophenylalanine on the conformations of small peptides. J. Am. Chem. Soc. 1995, 117 (13), 3808-3819; (i) Burgess, K.; Ho, K.-K.; Pettitt, B.M. J. Am. Chem. Soc. Conformational effects of substituting methionine with (2S,3S)-2,3-methanomethionine in Phe-Met-Arg-Phe-NH2. 1995, 117 (1), 54-65; (j) Balaji, V.N.; Ramnarayan, K.; Chan, M.-F.; Rao, S. Conformational studies on model peptides with 1-aminocyclopropane-1-carboxylic acid residues. Pep. Res. 1994, 7 (2), 60-71; (k) Burgess, K.; Ho, K.-K.; Pettitt, B.M. A γ-turn structure induced by 2S,3S-2,3-methanomethionine. J. Am. Chem. Soc. 1994, 116 (2), 799-800; (l) Mapelli, C.; Newton, M.G.; Ringold, C.E.; Stammer, C.H. Cyclopropane amino acid ester dipeptide sweeteners. Int. J. Peptide Protein Res. 1987, 30 (4), 498-510.
11. 1-conformations of phenylalanine. Chem. Eur. J. 1999, 5 (9), 2730-2739; (c) Jimenez, A.I.; Cativiela, C.; Aubry, A.; Marraud, M. β-Turn preferences induced by 2,3-methanophenylalanine chirality. J. Am. Chem. Soc. 1998, 120 (37), 9452-9459; (d) Moye-Sherman, D.; Jin, S.; Ham, I.; Burgess, K. Conformational preferences of RNase A C-peptide derivatives containing a highly constrained analog of phenylalanine. J. Am. Chem. Soc. 1998, 120 (37), 9435-9443; (e) Lim, D.; Burgess, K. Spirocyclic peptidomimetics featuring 2,3-methanoamino acids. J. Am. Chem. Soc. 1997, 119 (41), 9632-9640; (f) Jimenez, A.I.; Vandersse, R.; Marraud, M.; Aubry, A.; Cativiela, C. Folding types of dipeptides containing the diastereoisomeric cyclopropanic analogs of phenylalanine. Tetra. Lett. 1997, 38 (43), 7559-7562; (g) Burgess, K.; Ke, C.-Y. On the conformational bias of F((2R,3S)-cyclo-M)RFa induced by the cis-2,3-methanomethionine residue. J. Org. Chem. 1996, 61 (24), 8627-8631; (h) Burgess, K.; Ho, K.-K.; Pal, B. Comparison of the effects of (2S,3S)-2,3-methanomethionine, (2R,3R)-2,3-methano-methionine, and (2R,3R)-2,3-methanophenylalanine on the conformations of small peptides. J. Am. Chem. Soc. 1995, 117 (13), 3808-3819; (i) Burgess, K.; Ho, K.-K.; Pettitt, B.M. J. Am. Chem. Soc. Conformational effects of substituting methionine with (2S,3S)-2,3-methanomethionine in Phe-Met-Arg-Phe-NH2. 1995, 117 (1), 54-65; (j) Balaji, V.N.; Ramnarayan, K.; Chan, M.-F.; Rao, S. Conformational studies on model peptides with 1-aminocyclopropane-1-carboxylic acid residues. Pep. Res. 1994, 7 (2), 60-71; (k) Burgess, K.; Ho, K.-K.; Pettitt, B.M. A γ-turn structure induced by 2S,3S-2,3-methanomethionine. J. Am. Chem. Soc. 1994, 116 (2), 799-800; (l) Mapelli, C.; Newton, M.G.; Ringold, C.E.; Stammer, C.H. Cyclopropane amino acid ester dipeptide sweeteners. Int. J. Peptide Protein Res. 1987, 30 (4), 498-510.
12. 1-conformations of phenylalanine. Chem. Eur. J. 1999, 5 (9), 2730-2739; (c) Jimenez, A.I.; Cativiela, C.; Aubry, A.; Marraud, M. β-Turn preferences induced by 2,3-methanophenylalanine chirality. J. Am. Chem. Soc. 1998, 120 (37), 9452-9459; (d) Moye-Sherman, D.; Jin, S.; Ham, I.; Burgess, K. Conformational preferences of RNase A C-peptide derivatives containing a highly constrained analog of phenylalanine. J. Am. Chem. Soc. 1998, 120 (37), 9435-9443; (e) Lim, D.; Burgess, K. Spirocyclic peptidomimetics featuring 2,3-methanoamino acids. J. Am. Chem. Soc. 1997, 119 (41), 9632-9640; (f) Jimenez, A.I.; Vandersse, R.; Marraud, M.; Aubry, A.; Cativiela, C. Folding types of dipeptides containing the diastereoisomeric cyclopropanic analogs of phenylalanine. Tetra. Lett. 1997, 38 (43), 7559-7562; (g) Burgess, K.; Ke, C.-Y. On the conformational bias of F((2R,3S)-cyclo-M)RFa induced by the cis-2,3-methanomethionine residue. J. Org. Chem. 1996, 61 (24), 8627-8631; (h) Burgess, K.; Ho, K.-K.; Pal, B. Comparison of the effects of (2S,3S)-2,3-methanomethionine, (2R,3R)-2,3-methano-methionine, and (2R,3R)-2,3-methanophenylalanine on the conformations of small peptides. J. Am. Chem. Soc. 1995, 117 (13), 3808-3819; (i) Burgess, K.; Ho, K.-K.; Pettitt, B.M. J. Am. Chem. Soc. Conformational effects of substituting methionine with (2S,3S)-2,3-methanomethionine in Phe-Met-Arg-Phe-NH2. 1995, 117 (1), 54-65; (j) Balaji, V.N.; Ramnarayan, K.; Chan, M.-F.; Rao, S. Conformational studies on model peptides with 1-aminocyclopropane-1-carboxylic acid residues. Pep. Res. 1994, 7 (2), 60-71; (k) Burgess, K.; Ho, K.-K.; Pettitt, B.M. A γ-turn structure induced by 2S,3S-2,3-methanomethionine. J. Am. Chem. Soc. 1994, 116 (2), 799-800; (l) Mapelli, C.; Newton, M.G.; Ringold, C.E.; Stammer, C.H. Cyclopropane amino acid ester dipeptide sweeteners. Int. J. Peptide Protein Res. 1987, 30 (4), 498-510.
13. 1-conformations of phenylalanine. Chem. Eur. J. 1999, 5 (9), 2730-2739; (c) Jimenez, A.I.; Cativiela, C.; Aubry, A.; Marraud, M. β-Turn preferences induced by 2,3-methanophenylalanine chirality. J. Am. Chem. Soc. 1998, 120 (37), 9452-9459; (d) Moye-Sherman, D.; Jin, S.; Ham, I.; Burgess, K. Conformational preferences of RNase A C-peptide derivatives containing a highly constrained analog of phenylalanine. J. Am. Chem. Soc. 1998, 120 (37), 9435-9443; (e) Lim, D.; Burgess, K. Spirocyclic peptidomimetics featuring 2,3-methanoamino acids. J. Am. Chem. Soc. 1997, 119 (41), 9632-9640; (f) Jimenez, A.I.; Vandersse, R.; Marraud, M.; Aubry, A.; Cativiela, C. Folding types of dipeptides containing the diastereoisomeric cyclopropanic analogs of phenylalanine. Tetra. Lett. 1997, 38 (43), 7559-7562; (g) Burgess, K.; Ke, C.-Y. On the conformational bias of F((2R,3S)-cyclo-M)RFa induced by the cis-2,3-methanomethionine residue. J. Org. Chem. 1996, 61 (24), 8627-8631; (h) Burgess, K.; Ho, K.-K.; Pal, B. Comparison of the effects of (2S,3S)-2,3-methanomethionine, (2R,3R)-2,3-methano-methionine, and (2R,3R)-2,3-methanophenylalanine on the conformations of small peptides. J. Am. Chem. Soc. 1995, 117 (13), 3808-3819; (i) Burgess, K.; Ho, K.-K.; Pettitt, B.M. J. Am. Chem. Soc. Conformational effects of substituting methionine with (2S,3S)-2,3-methanomethionine in Phe-Met-Arg-Phe-NH2. 1995, 117 (1), 54-65; (j) Balaji, V.N.; Ramnarayan, K.; Chan, M.-F.; Rao, S. Conformational studies on model peptides with 1-aminocyclopropane-1-carboxylic acid residues. Pep. Res. 1994, 7 (2), 60-71; (k) Burgess, K.; Ho, K.-K.; Pettitt, B.M. A γ-turn structure induced by 2S,3S-2,3-methanomethionine. J. Am. Chem. Soc. 1994, 116 (2), 799-800; (l) Mapelli, C.; Newton, M.G.; Ringold, C.E.; Stammer, C.H. Cyclopropane amino acid ester dipeptide sweeteners. Int. J. Peptide Protein Res. 1987, 30 (4), 498-510.
14. 1-conformations of phenylalanine. Chem. Eur. J. 1999, 5 (9), 2730-2739; (c) Jimenez, A.I.; Cativiela, C.; Aubry, A.; Marraud, M. β-Turn preferences induced by 2,3-methanophenylalanine chirality. J. Am. Chem. Soc. 1998, 120 (37), 9452-9459; (d) Moye-Sherman, D.; Jin, S.; Ham, I.; Burgess, K. Conformational preferences of RNase A C-peptide derivatives containing a highly constrained analog of phenylalanine. J. Am. Chem. Soc. 1998, 120 (37), 9435-9443; (e) Lim, D.; Burgess, K. Spirocyclic peptidomimetics featuring 2,3-methanoamino acids. J. Am. Chem. Soc. 1997, 119 (41), 9632-9640; (f) Jimenez, A.I.; Vandersse, R.; Marraud, M.; Aubry, A.; Cativiela, C. Folding types of dipeptides containing the diastereoisomeric cyclopropanic analogs of phenylalanine. Tetra. Lett. 1997, 38 (43), 7559-7562; (g) Burgess, K.; Ke, C.-Y. On the conformational bias of F((2R,3S)-cyclo-M)RFa induced by the cis-2,3-methanomethionine residue. J. Org. Chem. 1996, 61 (24), 8627-8631; (h) Burgess, K.; Ho, K.-K.; Pal, B. Comparison of the effects of (2S,3S)-2,3-methanomethionine, (2R,3R)-2,3-methano-methionine, and (2R,3R)-2,3-methanophenylalanine on the conformations of small peptides. J. Am. Chem. Soc. 1995, 117 (13), 3808-3819; (i) Burgess, K.; Ho, K.-K.; Pettitt, B.M. J. Am. Chem. Soc. Conformational effects of substituting methionine with (2S,3S)-2,3-methanomethionine in Phe-Met-Arg-Phe-NH2. 1995, 117 (1), 54-65; (j) Balaji, V.N.; Ramnarayan, K.; Chan, M.-F.; Rao, S. Conformational studies on model peptides with 1-aminocyclopropane-1-carboxylic acid residues. Pep. Res. 1994, 7 (2), 60-71; (k) Burgess, K.; Ho, K.-K.; Pettitt, B.M. A γ-turn structure induced by 2S,3S-2,3-methanomethionine. J. Am. Chem. Soc. 1994, 116 (2), 799-800; (l) Mapelli, C.; Newton, M.G.; Ringold, C.E.; Stammer, C.H. Cyclopropane amino acid ester dipeptide sweeteners. Int. J. Peptide Protein Res. 1987, 30 (4), 498-510.
15. 1-conformations of phenylalanine. Chem. Eur. J. 1999, 5 (9), 2730-2739; (c) Jimenez, A.I.; Cativiela, C.; Aubry, A.; Marraud, M. β-Turn preferences induced by 2,3-methanophenylalanine chirality. J. Am. Chem. Soc. 1998, 120 (37), 9452-9459; (d) Moye-Sherman, D.; Jin, S.; Ham, I.; Burgess, K. Conformational preferences of RNase A C-peptide derivatives containing a highly constrained analog of phenylalanine. J. Am. Chem. Soc. 1998, 120 (37), 9435-9443; (e) Lim, D.; Burgess, K. Spirocyclic peptidomimetics featuring 2,3-methanoamino acids. J. Am. Chem. Soc. 1997, 119 (41), 9632-9640; (f) Jimenez, A.I.; Vandersse, R.; Marraud, M.; Aubry, A.; Cativiela, C. Folding types of dipeptides containing the diastereoisomeric cyclopropanic analogs of phenylalanine. Tetra. Lett. 1997, 38 (43), 7559-7562; (g) Burgess, K.; Ke, C.-Y. On the conformational bias of F((2R,3S)-cyclo-M)RFa induced by the cis-2,3-methanomethionine residue. J. Org. Chem. 1996, 61 (24), 8627-8631; (h) Burgess, K.; Ho, K.-K.; Pal, B. Comparison of the effects of (2S,3S)-2,3-methanomethionine, (2R,3R)-2,3-methano-methionine, and (2R,3R)-2,3-methanophenylalanine on the conformations of small peptides. J. Am. Chem. Soc. 1995, 117 (13), 3808-3819; (i) Burgess, K.; Ho, K.-K.; Pettitt, B.M. J. Am. Chem. Soc. Conformational effects of substituting methionine with (2S,3S)-2,3-methanomethionine in Phe-Met-Arg-Phe-NH2. 1995, 117 (1), 54-65; (j) Balaji, V.N.; Ramnarayan, K.; Chan, M.-F.; Rao, S. Conformational studies on model peptides with 1-aminocyclopropane-1-carboxylic acid residues. Pep. Res. 1994, 7 (2), 60-71; (k) Burgess, K.; Ho, K.-K.; Pettitt, B.M. A γ-turn structure induced by 2S,3S-2,3-methanomethionine. J. Am. Chem. Soc. 1994, 116 (2), 799-800; (l) Mapelli, C.; Newton, M.G.; Ringold, C.E.; Stammer, C.H. Cyclopropane amino acid ester dipeptide sweeteners. Int. J. Peptide Protein Res. 1987, 30 (4), 498-510.
16. 1-conformations of phenylalanine. Chem. Eur. J. 1999, 5 (9), 2730-2739; (c) Jimenez, A.I.; Cativiela, C.; Aubry, A.; Marraud, M. β-Turn preferences induced by 2,3-methanophenylalanine chirality. J. Am. Chem. Soc. 1998, 120 (37), 9452-9459; (d) Moye-Sherman, D.; Jin, S.; Ham, I.; Burgess, K. Conformational preferences of RNase A C-peptide derivatives containing a highly constrained analog of phenylalanine. J. Am. Chem. Soc. 1998, 120 (37), 9435-9443; (e) Lim, D.; Burgess, K. Spirocyclic peptidomimetics featuring 2,3-methanoamino acids. J. Am. Chem. Soc. 1997, 119 (41), 9632-9640; (f) Jimenez, A.I.; Vandersse, R.; Marraud, M.; Aubry, A.; Cativiela, C. Folding types of dipeptides containing the diastereoisomeric cyclopropanic analogs of phenylalanine. Tetra. Lett. 1997, 38 (43), 7559-7562; (g) Burgess, K.; Ke, C.-Y. On the conformational bias of F((2R,3S)-cyclo-M)RFa induced by the cis-2,3-methanomethionine residue. J. Org. Chem. 1996, 61 (24), 8627-8631; (h) Burgess, K.; Ho, K.-K.; Pal, B. Comparison of the effects of (2S,3S)-2,3-methanomethionine, (2R,3R)-2,3-methano-methionine, and (2R,3R)-2,3-methanophenylalanine on the conformations of small peptides. J. Am. Chem. Soc. 1995, 117 (13), 3808-3819; (i) Burgess, K.; Ho, K.-K.; Pettitt, B.M. J. Am. Chem. Soc. Conformational effects of substituting methionine with (2S,3S)-2,3-methanomethionine in Phe-Met-Arg-Phe-NH2. 1995, 117 (1), 54-65; (j) Balaji, V.N.; Ramnarayan, K.; Chan, M.-F.; Rao, S. Conformational studies on model peptides with 1-aminocyclopropane-1-carboxylic acid residues. Pep. Res. 1994, 7 (2), 60-71; (k) Burgess, K.; Ho, K.-K.; Pettitt, B.M. A γ-turn structure induced by 2S,3S-2,3-methanomethionine. J. Am. Chem. Soc. 1994, 116 (2), 799-800; (l) Mapelli, C.; Newton, M.G.; Ringold, C.E.; Stammer, C.H. Cyclopropane amino acid ester dipeptide sweeteners. Int. J. Peptide Protein Res. 1987, 30 (4), 498-510.
17. 1-conformations of phenylalanine. Chem. Eur. J. 1999, 5 (9), 2730-2739; (c) Jimenez, A.I.; Cativiela, C.; Aubry, A.; Marraud, M. β-Turn preferences induced by 2,3-methanophenylalanine chirality. J. Am. Chem. Soc. 1998, 120 (37), 9452-9459; (d) Moye-Sherman, D.; Jin, S.; Ham, I.; Burgess, K. Conformational preferences of RNase A C-peptide derivatives containing a highly constrained analog of phenylalanine. J. Am. Chem. Soc. 1998, 120 (37), 9435-9443; (e) Lim, D.; Burgess, K. Spirocyclic peptidomimetics featuring 2,3-methanoamino acids. J. Am. Chem. Soc. 1997, 119 (41), 9632-9640; (f) Jimenez, A.I.; Vandersse, R.; Marraud, M.; Aubry, A.; Cativiela, C. Folding types of dipeptides containing the diastereoisomeric cyclopropanic analogs of phenylalanine. Tetra. Lett. 1997, 38 (43), 7559-7562; (g) Burgess, K.; Ke, C.-Y. On the conformational bias of F((2R,3S)-cyclo-M)RFa induced by the cis-2,3-methanomethionine residue. J. Org. Chem. 1996, 61 (24), 8627-8631; (h) Burgess, K.; Ho, K.-K.; Pal, B. Comparison of the effects of (2S,3S)-2,3-methanomethionine, (2R,3R)-2,3-methano-methionine, and (2R,3R)-2,3-methanophenylalanine on the conformations of small peptides. J. Am. Chem. Soc. 1995, 117 (13), 3808-3819; (i) Burgess, K.; Ho, K.-K.; Pettitt, B.M. J. Am. Chem. Soc. Conformational effects of substituting methionine with (2S,3S)-2,3-methanomethionine in Phe-Met-Arg-Phe-NH2. 1995, 117 (1), 54-65; (j) Balaji, V.N.; Ramnarayan, K.; Chan, M.-F.; Rao, S. Conformational studies on model peptides with 1-aminocyclopropane-1-carboxylic acid residues. Pep. Res. 1994, 7 (2), 60-71; (k) Burgess, K.; Ho, K.-K.; Pettitt, B.M. A γ-turn structure induced by 2S,3S-2,3-methanomethionine. J. Am. Chem. Soc. 1994, 116 (2), 799-800; (l) Mapelli, C.; Newton, M.G.; Ringold, C.E.; Stammer, C.H. Cyclopropane amino acid ester dipeptide sweeteners. Int. J. Peptide Protein Res. 1987, 30 (4), 498-510.
18. 1-conformations of phenylalanine. Chem. Eur. J. 1999, 5 (9), 2730-2739; (c) Jimenez, A.I.; Cativiela, C.; Aubry, A.; Marraud, M. β-Turn preferences induced by 2,3-methanophenylalanine chirality. J. Am. Chem. Soc. 1998, 120 (37), 9452-9459; (d) Moye-Sherman, D.; Jin, S.; Ham, I.; Burgess, K. Conformational preferences of RNase A C-peptide derivatives containing a highly constrained analog of phenylalanine. J. Am. Chem. Soc. 1998, 120 (37), 9435-9443; (e) Lim, D.; Burgess, K. Spirocyclic peptidomimetics featuring 2,3-methanoamino acids. J. Am. Chem. Soc. 1997, 119 (41), 9632-9640; (f) Jimenez, A.I.; Vandersse, R.; Marraud, M.; Aubry, A.; Cativiela, C. Folding types of dipeptides containing the diastereoisomeric cyclopropanic analogs of phenylalanine. Tetra. Lett. 1997, 38 (43), 7559-7562; (g) Burgess, K.; Ke, C.-Y. On the conformational bias of F((2R,3S)-cyclo-M)RFa induced by the cis-2,3-methanomethionine residue. J. Org. Chem. 1996, 61 (24), 8627-8631; (h) Burgess, K.; Ho, K.-K.; Pal, B. Comparison of the effects of (2S,3S)-2,3-methanomethionine, (2R,3R)-2,3-methano-methionine, and (2R,3R)-2,3-methanophenylalanine on the conformations of small peptides. J. Am. Chem. Soc. 1995, 117 (13), 3808-3819; (i) Burgess, K.; Ho, K.-K.; Pettitt, B.M. J. Am. Chem. Soc. Conformational effects of substituting methionine with (2S,3S)-2,3-methanomethionine in Phe-Met-Arg-Phe-NH2. 1995, 117 (1), 54-65; (j) Balaji, V.N.; Ramnarayan, K.; Chan, M.-F.; Rao, S. Conformational studies on model peptides with 1-aminocyclopropane-1-carboxylic acid residues. Pep. Res. 1994, 7 (2), 60-71; (k) Burgess, K.; Ho, K.-K.; Pettitt, B.M. A γ-turn structure induced by 2S,3S-2,3-methanomethionine. J. Am. Chem. Soc. 1994, 116 (2), 799-800; (l) Mapelli, C.; Newton, M.G.; Ringold, C.E.; Stammer, C.H. Cyclopropane amino acid ester dipeptide sweeteners. Int. J. Peptide Protein Res. 1987, 30 (4), 498-510.
19. For some selected recent examples about the synthesis of 2-substituted or 2,2-disubstituted ACCs, see: (a) Abellan, T.; Mancheno, B.; Najera, C.; Sansano, J.M. Asymmetric synthesis of α-amino acids from α,β-(Z)-didehydroamino acid derivatives with 1,2,3,6-tetra-hydropyrazin-2-one structure. Tetrahedron 2001, 57 (30), 6627-6640; (b) Clerici, F.; Gelmi, M.L.; Pocar, D.; Pilati, T. Masked constrained cysteines: diastereoselective and enantioselective synthesis of 1-amino-2-mercaptocyclo-propanecarboxylic acid derivatives. Tetrahedron: Asymmetry 2001, 12 (19), 2663-2669; (c) Salgado, A.; Huybrechts, T.; Eeckhaut, A.; Van der Eycken, J.; Szakonyi, Z.; Fulop, F.; Tkachev, A.; De Kimpe, N. Synthesis of (1S)-1-amino-2,2-dimethylcyclopropane-1-carboxylic acid via PLE mediated hydrolysis of bis(2,2,2-trifluoroethyl)-2,2-dimethylcyclopropane-1,1-dicarboxylate. Tetrahedron 2001, 57 (14), 2781-2786; (d) Debache, A.; Collet, S.; Bauchat, P.; Danion, D.; Euzenat, L.; Hercouet, A.; Carboni, B. Belokon's Ni(II) complex as a chiral masked glycine for the diastereoselective synthesis of 2-substituted 1-aminocyclo-propane carboxylic acids. Tetrahedron: Asymmetry 2001, 12 (5), 761-764; (e) Racouchot, S.; Ollivier, J.; Salaun, J. Titanium-mediated diastereoselective formation of (Z)-1-(1-alkenyl)-2-substituted-cyclopropyl esters efficient precursors of (Z)-2,3-methanoamino acids. Synlett 2000, 12, 1729-1732; (f) Abellan, T.; Chinchilla, R.; Galindo, N.; Najera, C.; Sansano, J.M. New oxazinone and pyrazinone derivatives as chiral reagents for the asymmetric synthesis of α-amino acids. J. Heterocyclic Chem. 2000, 37 (3), 467-479; (g) Katagiri, T.; Irie, M.; Minoru, U.K. Syntheses of optically active trifluoronorcoronamic acids. Org. Lett. 2000, 2 (16), 2423-2425; (h) Donkor, I.O.; Zheng, X.; Han, J.; Miller, D.D. Asymmetric synthesis of 2,3-methanoleucine stereoisomers from common intermediates. Chirality 2000, 12, 551-557; (i) Chinchilla, R.; Falvello, L.R.; Galindo, N.; Najera, C. New chiral didehydroamino acid derivatives from a cyclic glycine template with 3,6-dihydro-2H-1,4-oxazin-2-one structure: applications to the asymmetric synthesis of nonproteinogenic α-amino acids. J. Org. Chem. 2000, 65 (10), 3034-3041; (j) Kordes, M.; Winsel, H.; de Meijere, A. Cyclopropyl building blocks for organic synthesis 58; A new short access to amino acids incorporating an aminocyclopropyl moiety from N,N-dibenzyl-carboxamides. Eur. J. Org. Chem. 2000, 18, 3235-3245; (k) Kozyrkov, Y.; Pukin, A.; Kulinkovich, O.; Ollivier, J.; Salaun, J. A convenient approach to substituted 1-(1-alkenyl)cyclopropanols: a new preparation of 2,3-methano amino acids. Tetrahedron Lett. 2000, 41 (33), 6399-6402; (l) Dorizon, P.; Su, G.; Ludvig, G.; Nikitina, L.; Paugam, R.; Ollivier, J.; Salaun, J. Stereoselective synthesis of highly functionalized cyclopropanes. Application to the asymmetric synthesis of (1S,2S)-2,3-methanoamino acids. J. Org. Chem. 1999, 64 (13), 4712-4724.
20. For some selected recent examples about the synthesis of 2-substituted or 2,2-disubstituted ACCs, see: (a) Abellan, T.; Mancheno, B.; Najera, C.; Sansano, J.M. Asymmetric synthesis of α-amino acids from α,β-(Z)-didehydroamino acid derivatives with 1,2,3,6-tetra-hydropyrazin-2-one structure. Tetrahedron 2001, 57 (30), 6627-6640; (b) Clerici, F.; Gelmi, M.L.; Pocar, D.; Pilati, T. Masked constrained cysteines: diastereoselective and enantioselective synthesis of 1-amino-2-mercaptocyclo-propanecarboxylic acid derivatives. Tetrahedron: Asymmetry 2001, 12 (19), 2663-2669; (c) Salgado, A.; Huybrechts, T.; Eeckhaut, A.; Van der Eycken, J.; Szakonyi, Z.; Fulop, F.; Tkachev, A.; De Kimpe, N. Synthesis of (1S)-1-amino-2,2-dimethylcyclopropane-1-carboxylic acid via PLE mediated hydrolysis of bis(2,2,2-trifluoroethyl)-2,2-dimethylcyclopropane-1,1-dicarboxylate. Tetrahedron 2001, 57 (14), 2781-2786; (d) Debache, A.; Collet, S.; Bauchat, P.; Danion, D.; Euzenat, L.; Hercouet, A.; Carboni, B. Belokon's Ni(II) complex as a chiral masked glycine for the diastereoselective synthesis of 2-substituted 1-aminocyclo-propane carboxylic acids. Tetrahedron: Asymmetry 2001, 12 (5), 761-764; (e) Racouchot, S.; Ollivier, J.; Salaun, J. Titanium-mediated diastereoselective formation of (Z)-1-(1-alkenyl)-2-substituted-cyclopropyl esters efficient precursors of (Z)-2,3-methanoamino acids. Synlett 2000, 12, 1729-1732; (f) Abellan, T.; Chinchilla, R.; Galindo, N.; Najera, C.; Sansano, J.M. New oxazinone and pyrazinone derivatives as chiral reagents for the asymmetric synthesis of α-amino acids. J. Heterocyclic Chem. 2000, 37 (3), 467-479; (g) Katagiri, T.; Irie, M.; Minoru, U.K. Syntheses of optically active trifluoronorcoronamic acids. Org. Lett. 2000, 2 (16), 2423-2425; (h) Donkor, I.O.; Zheng, X.; Han, J.; Miller, D.D. Asymmetric synthesis of 2,3-methanoleucine stereoisomers from common intermediates. Chirality 2000, 12, 551-557; (i) Chinchilla, R.; Falvello, L.R.; Galindo, N.; Najera, C. New chiral didehydroamino acid derivatives from a cyclic glycine template with 3,6-dihydro-2H-1,4-oxazin-2-one structure: applications to the asymmetric synthesis of nonproteinogenic α-amino acids. J. Org. Chem. 2000, 65 (10), 3034-3041; (j) Kordes, M.; Winsel, H.; de Meijere, A. Cyclopropyl building blocks for organic synthesis 58; A new short access to amino acids incorporating an aminocyclopropyl moiety from N,N-dibenzyl-carboxamides. Eur. J. Org. Chem. 2000, 18, 3235-3245; (k) Kozyrkov, Y.; Pukin, A.; Kulinkovich, O.; Ollivier, J.; Salaun, J. A convenient approach to substituted 1-(1-alkenyl)cyclopropanols: a new preparation of 2,3-methano amino acids. Tetrahedron Lett. 2000, 41 (33), 6399-6402; (l) Dorizon, P.; Su, G.; Ludvig, G.; Nikitina, L.; Paugam, R.; Ollivier, J.; Salaun, J. Stereoselective synthesis of highly functionalized cyclopropanes. Application to the asymmetric synthesis of (1S,2S)-2,3-methanoamino acids. J. Org. Chem. 1999, 64 (13), 4712-4724.
21. For some selected recent examples about the synthesis of 2-substituted or 2,2-disubstituted ACCs, see: (a) Abellan, T.; Mancheno, B.; Najera, C.; Sansano, J.M. Asymmetric synthesis of α-amino acids from α,β-(Z)-didehydroamino acid derivatives with 1,2,3,6-tetra-hydropyrazin-2-one structure. Tetrahedron 2001, 57 (30), 6627-6640; (b) Clerici, F.; Gelmi, M.L.; Pocar, D.; Pilati, T. Masked constrained cysteines: diastereoselective and enantioselective synthesis of 1-amino-2-mercaptocyclo-propanecarboxylic acid derivatives. Tetrahedron: Asymmetry 2001, 12 (19), 2663-2669; (c) Salgado, A.; Huybrechts, T.; Eeckhaut, A.; Van der Eycken, J.; Szakonyi, Z.; Fulop, F.; Tkachev, A.; De Kimpe, N. Synthesis of (1S)-1-amino-2,2-dimethylcyclopropane-1-carboxylic acid via PLE mediated hydrolysis of bis(2,2,2-trifluoroethyl)-2,2-dimethylcyclopropane-1,1-dicarboxylate. Tetrahedron 2001, 57 (14), 2781-2786; (d) Debache, A.; Collet, S.; Bauchat, P.; Danion, D.; Euzenat, L.; Hercouet, A.; Carboni, B. Belokon's Ni(II) complex as a chiral masked glycine for the diastereoselective synthesis of 2-substituted 1-aminocyclo-propane carboxylic acids. Tetrahedron: Asymmetry 2001, 12 (5), 761-764; (e) Racouchot, S.; Ollivier, J.; Salaun, J. Titanium-mediated diastereoselective formation of (Z)-1-(1-alkenyl)-2-substituted-cyclopropyl esters efficient precursors of (Z)-2,3-methanoamino acids. Synlett 2000, 12, 1729-1732; (f) Abellan, T.; Chinchilla, R.; Galindo, N.; Najera, C.; Sansano, J.M. New oxazinone and pyrazinone derivatives as chiral reagents for the asymmetric synthesis of α-amino acids. J. Heterocyclic Chem. 2000, 37 (3), 467-479; (g) Katagiri, T.; Irie, M.; Minoru, U.K. Syntheses of optically active trifluoronorcoronamic acids. Org. Lett. 2000, 2 (16), 2423-2425; (h) Donkor, I.O.; Zheng, X.; Han, J.; Miller, D.D. Asymmetric synthesis of 2,3-methanoleucine stereoisomers from common intermediates. Chirality 2000, 12, 551-557; (i) Chinchilla, R.; Falvello, L.R.; Galindo, N.; Najera, C. New chiral didehydroamino acid derivatives from a cyclic glycine template with 3,6-dihydro-2H-1,4-oxazin-2-one structure: applications to the asymmetric synthesis of nonproteinogenic α-amino acids. J. Org. Chem. 2000, 65 (10), 3034-3041; (j) Kordes, M.; Winsel, H.; de Meijere, A. Cyclopropyl building blocks for organic synthesis 58; A new short access to amino acids incorporating an aminocyclopropyl moiety from N,N-dibenzyl-carboxamides. Eur. J. Org. Chem. 2000, 18, 3235-3245; (k) Kozyrkov, Y.; Pukin, A.; Kulinkovich, O.; Ollivier, J.; Salaun, J. A convenient approach to substituted 1-(1-alkenyl)cyclopropanols: a new preparation of 2,3-methano amino acids. Tetrahedron Lett. 2000, 41 (33), 6399-6402; (l) Dorizon, P.; Su, G.; Ludvig, G.; Nikitina, L.; Paugam, R.; Ollivier, J.; Salaun, J. Stereoselective synthesis of highly functionalized cyclopropanes. Application to the asymmetric synthesis of (1S,2S)-2,3-methanoamino acids. J. Org. Chem. 1999, 64 (13), 4712-4724.
22. For some selected recent examples about the synthesis of 2-substituted or 2,2-disubstituted ACCs, see: (a) Abellan, T.; Mancheno, B.; Najera, C.; Sansano, J.M. Asymmetric synthesis of α-amino acids from α,β-(Z)-didehydroamino acid derivatives with 1,2,3,6-tetra-hydropyrazin-2-one structure. Tetrahedron 2001, 57 (30), 6627-6640; (b) Clerici, F.; Gelmi, M.L.; Pocar, D.; Pilati, T. Masked constrained cysteines: diastereoselective and enantioselective synthesis of 1-amino-2-mercaptocyclo-propanecarboxylic acid derivatives. Tetrahedron: Asymmetry 2001, 12 (19), 2663-2669; (c) Salgado, A.; Huybrechts, T.; Eeckhaut, A.; Van der Eycken, J.; Szakonyi, Z.; Fulop, F.; Tkachev, A.; De Kimpe, N. Synthesis of (1S)-1-amino-2,2-dimethylcyclopropane-1-carboxylic acid via PLE mediated hydrolysis of bis(2,2,2-trifluoroethyl)-2,2-dimethylcyclopropane-1,1-dicarboxylate. Tetrahedron 2001, 57 (14), 2781-2786; (d) Debache, A.; Collet, S.; Bauchat, P.; Danion, D.; Euzenat, L.; Hercouet, A.; Carboni, B. Belokon's Ni(II) complex as a chiral masked glycine for the diastereoselective synthesis of 2-substituted 1-aminocyclo-propane carboxylic acids. Tetrahedron: Asymmetry 2001, 12 (5), 761-764; (e) Racouchot, S.; Ollivier, J.; Salaun, J. Titanium-mediated diastereoselective formation of (Z)-1-(1-alkenyl)-2-substituted-cyclopropyl esters efficient precursors of (Z)-2,3-methanoamino acids. Synlett 2000, 12, 1729-1732; (f) Abellan, T.; Chinchilla, R.; Galindo, N.; Najera, C.; Sansano, J.M. New oxazinone and pyrazinone derivatives as chiral reagents for the asymmetric synthesis of α-amino acids. J. Heterocyclic Chem. 2000, 37 (3), 467-479; (g) Katagiri, T.; Irie, M.; Minoru, U.K. Syntheses of optically active trifluoronorcoronamic acids. Org. Lett. 2000, 2 (16), 2423-2425; (h) Donkor, I.O.; Zheng, X.; Han, J.; Miller, D.D. Asymmetric synthesis of 2,3-methanoleucine stereoisomers from common intermediates. Chirality 2000, 12, 551-557; (i) Chinchilla, R.; Falvello, L.R.; Galindo, N.; Najera, C. New chiral didehydroamino acid derivatives from a cyclic glycine template with 3,6-dihydro-2H-1,4-oxazin-2-one structure: applications to the asymmetric synthesis of nonproteinogenic α-amino acids. J. Org. Chem. 2000, 65 (10), 3034-3041; (j) Kordes, M.; Winsel, H.; de Meijere, A. Cyclopropyl building blocks for organic synthesis 58; A new short access to amino acids incorporating an aminocyclopropyl moiety from N,N-dibenzyl-carboxamides. Eur. J. Org. Chem. 2000, 18, 3235-3245; (k) Kozyrkov, Y.; Pukin, A.; Kulinkovich, O.; Ollivier, J.; Salaun, J. A convenient approach to substituted 1-(1-alkenyl)cyclopropanols: a new preparation of 2,3-methano amino acids. Tetrahedron Lett. 2000, 41 (33), 6399-6402; (l) Dorizon, P.; Su, G.; Ludvig, G.; Nikitina, L.; Paugam, R.; Ollivier, J.; Salaun, J. Stereoselective synthesis of highly functionalized cyclopropanes. Application to the asymmetric synthesis of (1S,2S)-2,3-methanoamino acids. J. Org. Chem. 1999, 64 (13), 4712-4724.
23. For some selected recent examples about the synthesis of 2-substituted or 2,2-disubstituted ACCs, see: (a) Abellan, T.; Mancheno, B.; Najera, C.; Sansano, J.M. Asymmetric synthesis of α-amino acids from α,β-(Z)-didehydroamino acid derivatives with 1,2,3,6-tetra-hydropyrazin-2-one structure. Tetrahedron 2001, 57 (30), 6627-6640; (b) Clerici, F.; Gelmi, M.L.; Pocar, D.; Pilati, T. Masked constrained cysteines: diastereoselective and enantioselective synthesis of 1-amino-2-mercaptocyclo-propanecarboxylic acid derivatives. Tetrahedron: Asymmetry 2001, 12 (19), 2663-2669; (c) Salgado, A.; Huybrechts, T.; Eeckhaut, A.; Van der Eycken, J.; Szakonyi, Z.; Fulop, F.; Tkachev, A.; De Kimpe, N. Synthesis of (1S)-1-amino-2,2-dimethylcyclopropane-1-carboxylic acid via PLE mediated hydrolysis of bis(2,2,2-trifluoroethyl)-2,2-dimethylcyclopropane-1,1-dicarboxylate. Tetrahedron 2001, 57 (14), 2781-2786; (d) Debache, A.; Collet, S.; Bauchat, P.; Danion, D.; Euzenat, L.; Hercouet, A.; Carboni, B. Belokon's Ni(II) complex as a chiral masked glycine for the diastereoselective synthesis of 2-substituted 1-aminocyclo-propane carboxylic acids. Tetrahedron: Asymmetry 2001, 12 (5), 761-764; (e) Racouchot, S.; Ollivier, J.; Salaun, J. Titanium-mediated diastereoselective formation of (Z)-1-(1-alkenyl)-2-substituted-cyclopropyl esters efficient precursors of (Z)-2,3-methanoamino acids. Synlett 2000, 12, 1729-1732; (f) Abellan, T.; Chinchilla, R.; Galindo, N.; Najera, C.; Sansano, J.M. New oxazinone and pyrazinone derivatives as chiral reagents for the asymmetric synthesis of α-amino acids. J. Heterocyclic Chem. 2000, 37 (3), 467-479; (g) Katagiri, T.; Irie, M.; Minoru, U.K. Syntheses of optically active trifluoronorcoronamic acids. Org. Lett. 2000, 2 (16), 2423-2425; (h) Donkor, I.O.; Zheng, X.; Han, J.; Miller, D.D. Asymmetric synthesis of 2,3-methanoleucine stereoisomers from common intermediates. Chirality 2000, 12, 551-557; (i) Chinchilla, R.; Falvello, L.R.; Galindo, N.; Najera, C. New chiral didehydroamino acid derivatives from a cyclic glycine template with 3,6-dihydro-2H-1,4-oxazin-2-one structure: applications to the asymmetric synthesis of nonproteinogenic α-amino acids. J. Org. Chem. 2000, 65 (10), 3034-3041; (j) Kordes, M.; Winsel, H.; de Meijere, A. Cyclopropyl building blocks for organic synthesis 58; A new short access to amino acids incorporating an aminocyclopropyl moiety from N,N-dibenzyl-carboxamides. Eur. J. Org. Chem. 2000, 18, 3235-3245; (k) Kozyrkov, Y.; Pukin, A.; Kulinkovich, O.; Ollivier, J.; Salaun, J. A convenient approach to substituted 1-(1-alkenyl)cyclopropanols: a new preparation of 2,3-methano amino acids. Tetrahedron Lett. 2000, 41 (33), 6399-6402; (l) Dorizon, P.; Su, G.; Ludvig, G.; Nikitina, L.; Paugam, R.; Ollivier, J.; Salaun, J. Stereoselective synthesis of highly functionalized cyclopropanes. Application to the asymmetric synthesis of (1S,2S)-2,3-methanoamino acids. J. Org. Chem. 1999, 64 (13), 4712-4724.
24. For some selected recent examples about the synthesis of 2-substituted or 2,2-disubstituted ACCs, see: (a) Abellan, T.; Mancheno, B.; Najera, C.; Sansano, J.M. Asymmetric synthesis of α-amino acids from α,β-(Z)-didehydroamino acid derivatives with 1,2,3,6-tetra-hydropyrazin-2-one structure. Tetrahedron 2001, 57 (30), 6627-6640; (b) Clerici, F.; Gelmi, M.L.; Pocar, D.; Pilati, T. Masked constrained cysteines: diastereoselective and enantioselective synthesis of 1-amino-2-mercaptocyclo-propanecarboxylic acid derivatives. Tetrahedron: Asymmetry 2001, 12 (19), 2663-2669; (c) Salgado, A.; Huybrechts, T.; Eeckhaut, A.; Van der Eycken, J.; Szakonyi, Z.; Fulop, F.; Tkachev, A.; De Kimpe, N. Synthesis of (1S)-1-amino-2,2-dimethylcyclopropane-1-carboxylic acid via PLE mediated hydrolysis of bis(2,2,2-trifluoroethyl)-2,2-dimethylcyclopropane-1,1-dicarboxylate. Tetrahedron 2001, 57 (14), 2781-2786; (d) Debache, A.; Collet, S.; Bauchat, P.; Danion, D.; Euzenat, L.; Hercouet, A.; Carboni, B. Belokon's Ni(II) complex as a chiral masked glycine for the diastereoselective synthesis of 2-substituted 1-aminocyclo-propane carboxylic acids. Tetrahedron: Asymmetry 2001, 12 (5), 761-764; (e) Racouchot, S.; Ollivier, J.; Salaun, J. Titanium-mediated diastereoselective formation of (Z)-1-(1-alkenyl)-2-substituted-cyclopropyl esters efficient precursors of (Z)-2,3-methanoamino acids. Synlett 2000, 12, 1729-1732; (f) Abellan, T.; Chinchilla, R.; Galindo, N.; Najera, C.; Sansano, J.M. New oxazinone and pyrazinone derivatives as chiral reagents for the asymmetric synthesis of α-amino acids. J. Heterocyclic Chem. 2000, 37 (3), 467-479; (g) Katagiri, T.; Irie, M.; Minoru, U.K. Syntheses of optically active trifluoronorcoronamic acids. Org. Lett. 2000, 2 (16), 2423-2425; (h) Donkor, I.O.; Zheng, X.; Han, J.; Miller, D.D. Asymmetric synthesis of 2,3-methanoleucine stereoisomers from common intermediates. Chirality 2000, 12, 551-557; (i) Chinchilla, R.; Falvello, L.R.; Galindo, N.; Najera, C. New chiral didehydroamino acid derivatives from a cyclic glycine template with 3,6-dihydro-2H-1,4-oxazin-2-one structure: applications to the asymmetric synthesis of nonproteinogenic α-amino acids. J. Org. Chem. 2000, 65 (10), 3034-3041; (j) Kordes, M.; Winsel, H.; de Meijere, A. Cyclopropyl building blocks for organic synthesis 58; A new short access to amino acids incorporating an aminocyclopropyl moiety from N,N-dibenzyl-carboxamides. Eur. J. Org. Chem. 2000, 18, 3235-3245; (k) Kozyrkov, Y.; Pukin, A.; Kulinkovich, O.; Ollivier, J.; Salaun, J. A convenient approach to substituted 1-(1-alkenyl)cyclopropanols: a new preparation of 2,3-methano amino acids. Tetrahedron Lett. 2000, 41 (33), 6399-6402; (l) Dorizon, P.; Su, G.; Ludvig, G.; Nikitina, L.; Paugam, R.; Ollivier, J.; Salaun, J. Stereoselective synthesis of highly functionalized cyclopropanes. Application to the asymmetric synthesis of (1S,2S)-2,3-methanoamino acids. J. Org. Chem. 1999, 64 (13), 4712-4724.
25. For some selected recent examples about the synthesis of 2-substituted or 2,2-disubstituted ACCs, see: (a) Abellan, T.; Mancheno, B.; Najera, C.; Sansano, J.M. Asymmetric synthesis of α-amino acids from α,β-(Z)-didehydroamino acid derivatives with 1,2,3,6-tetra-hydropyrazin-2-one structure. Tetrahedron 2001, 57 (30), 6627-6640; (b) Clerici, F.; Gelmi, M.L.; Pocar, D.; Pilati, T. Masked constrained cysteines: diastereoselective and enantioselective synthesis of 1-amino-2-mercaptocyclo-propanecarboxylic acid derivatives. Tetrahedron: Asymmetry 2001, 12 (19), 2663-2669; (c) Salgado, A.; Huybrechts, T.; Eeckhaut, A.; Van der Eycken, J.; Szakonyi, Z.; Fulop, F.; Tkachev, A.; De Kimpe, N. Synthesis of (1S)-1-amino-2,2-dimethylcyclopropane-1-carboxylic acid via PLE mediated hydrolysis of bis(2,2,2-trifluoroethyl)-2,2-dimethylcyclopropane-1,1-dicarboxylate. Tetrahedron 2001, 57 (14), 2781-2786; (d) Debache, A.; Collet, S.; Bauchat, P.; Danion, D.; Euzenat, L.; Hercouet, A.; Carboni, B. Belokon's Ni(II) complex as a chiral masked glycine for the diastereoselective synthesis of 2-substituted 1-aminocyclo-propane carboxylic acids. Tetrahedron: Asymmetry 2001, 12 (5), 761-764; (e) Racouchot, S.; Ollivier, J.; Salaun, J. Titanium-mediated diastereoselective formation of (Z)-1-(1-alkenyl)-2-substituted-cyclopropyl esters efficient precursors of (Z)-2,3-methanoamino acids. Synlett 2000, 12, 1729-1732; (f) Abellan, T.; Chinchilla, R.; Galindo, N.; Najera, C.; Sansano, J.M. New oxazinone and pyrazinone derivatives as chiral reagents for the asymmetric synthesis of α-amino acids. J. Heterocyclic Chem. 2000, 37 (3), 467-479; (g) Katagiri, T.; Irie, M.; Minoru, U.K. Syntheses of optically active trifluoronorcoronamic acids. Org. Lett. 2000, 2 (16), 2423-2425; (h) Donkor, I.O.; Zheng, X.; Han, J.; Miller, D.D. Asymmetric synthesis of 2,3-methanoleucine stereoisomers from common intermediates. Chirality 2000, 12, 551-557; (i) Chinchilla, R.; Falvello, L.R.; Galindo, N.; Najera, C. New chiral didehydroamino acid derivatives from a cyclic glycine template with 3,6-dihydro-2H-1,4-oxazin-2-one structure: applications to the asymmetric synthesis of nonproteinogenic α-amino acids. J. Org. Chem. 2000, 65 (10), 3034-3041; (j) Kordes, M.; Winsel, H.; de Meijere, A. Cyclopropyl building blocks for organic synthesis 58; A new short access to amino acids incorporating an aminocyclopropyl moiety from N,N-dibenzyl-carboxamides. Eur. J. Org. Chem. 2000, 18, 3235-3245; (k) Kozyrkov, Y.; Pukin, A.; Kulinkovich, O.; Ollivier, J.; Salaun, J. A convenient approach to substituted 1-(1-alkenyl)cyclopropanols: a new preparation of 2,3-methano amino acids. Tetrahedron Lett. 2000, 41 (33), 6399-6402; (l) Dorizon, P.; Su, G.; Ludvig, G.; Nikitina, L.; Paugam, R.; Ollivier, J.; Salaun, J. Stereoselective synthesis of highly functionalized cyclopropanes. Application to the asymmetric synthesis of (1S,2S)-2,3-methanoamino acids. J. Org. Chem. 1999, 64 (13), 4712-4724.
26. For some selected recent examples about the synthesis of 2-substituted or 2,2-disubstituted ACCs, see: (a) Abellan, T.; Mancheno, B.; Najera, C.; Sansano, J.M. Asymmetric synthesis of α-amino acids from α,β-(Z)-didehydroamino acid derivatives with 1,2,3,6-tetra-hydropyrazin-2-one structure. Tetrahedron 2001, 57 (30), 6627-6640; (b) Clerici, F.; Gelmi, M.L.; Pocar, D.; Pilati, T. Masked constrained cysteines: diastereoselective and enantioselective synthesis of 1-amino-2-mercaptocyclo-propanecarboxylic acid derivatives. Tetrahedron: Asymmetry 2001, 12 (19), 2663-2669; (c) Salgado, A.; Huybrechts, T.; Eeckhaut, A.; Van der Eycken, J.; Szakonyi, Z.; Fulop, F.; Tkachev, A.; De Kimpe, N. Synthesis of (1S)-1-amino-2,2-dimethylcyclopropane-1-carboxylic acid via PLE mediated hydrolysis of bis(2,2,2-trifluoroethyl)-2,2-dimethylcyclopropane-1,1-dicarboxylate. Tetrahedron 2001, 57 (14), 2781-2786; (d) Debache, A.; Collet, S.; Bauchat, P.; Danion, D.; Euzenat, L.; Hercouet, A.; Carboni, B. Belokon's Ni(II) complex as a chiral masked glycine for the diastereoselective synthesis of 2-substituted 1-aminocyclo-propane carboxylic acids. Tetrahedron: Asymmetry 2001, 12 (5), 761-764; (e) Racouchot, S.; Ollivier, J.; Salaun, J. Titanium-mediated diastereoselective formation of (Z)-1-(1-alkenyl)-2-substituted-cyclopropyl esters efficient precursors of (Z)-2,3-methanoamino acids. Synlett 2000, 12, 1729-1732; (f) Abellan, T.; Chinchilla, R.; Galindo, N.; Najera, C.; Sansano, J.M. New oxazinone and pyrazinone derivatives as chiral reagents for the asymmetric synthesis of α-amino acids. J. Heterocyclic Chem. 2000, 37 (3), 467-479; (g) Katagiri, T.; Irie, M.; Minoru, U.K. Syntheses of optically active trifluoronorcoronamic acids. Org. Lett. 2000, 2 (16), 2423-2425; (h) Donkor, I.O.; Zheng, X.; Han, J.; Miller, D.D. Asymmetric synthesis of 2,3-methanoleucine stereoisomers from common intermediates. Chirality 2000, 12, 551-557; (i) Chinchilla, R.; Falvello, L.R.; Galindo, N.; Najera, C. New chiral didehydroamino acid derivatives from a cyclic glycine template with 3,6-dihydro-2H-1,4-oxazin-2-one structure: applications to the asymmetric synthesis of nonproteinogenic α-amino acids. J. Org. Chem. 2000, 65 (10), 3034-3041; (j) Kordes, M.; Winsel, H.; de Meijere, A. Cyclopropyl building blocks for organic synthesis 58; A new short access to amino acids incorporating an aminocyclopropyl moiety from N,N-dibenzyl-carboxamides. Eur. J. Org. Chem. 2000, 18, 3235-3245; (k) Kozyrkov, Y.; Pukin, A.; Kulinkovich, O.; Ollivier, J.; Salaun, J. A convenient approach to substituted 1-(1-alkenyl)cyclopropanols: a new preparation of 2,3-methano amino acids. Tetrahedron Lett. 2000, 41 (33), 6399-6402; (l) Dorizon, P.; Su, G.; Ludvig, G.; Nikitina, L.; Paugam, R.; Ollivier, J.; Salaun, J. Stereoselective synthesis of highly functionalized cyclopropanes. Application to the asymmetric synthesis of (1S,2S)-2,3-methanoamino acids. J. Org. Chem. 1999, 64 (13), 4712-4724.
27. For some selected recent examples about the synthesis of 2-substituted or 2,2-disubstituted ACCs, see: (a) Abellan, T.; Mancheno, B.; Najera, C.; Sansano, J.M. Asymmetric synthesis of α-amino acids from α,β-(Z)-didehydroamino acid derivatives with 1,2,3,6-tetra-hydropyrazin-2-one structure. Tetrahedron 2001, 57 (30), 6627-6640; (b) Clerici, F.; Gelmi, M.L.; Pocar, D.; Pilati, T. Masked constrained cysteines: diastereoselective and enantioselective synthesis of 1-amino-2-mercaptocyclo-propanecarboxylic acid derivatives. Tetrahedron: Asymmetry 2001, 12 (19), 2663-2669; (c) Salgado, A.; Huybrechts, T.; Eeckhaut, A.; Van der Eycken, J.; Szakonyi, Z.; Fulop, F.; Tkachev, A.; De Kimpe, N. Synthesis of (1S)-1-amino-2,2-dimethylcyclopropane-1-carboxylic acid via PLE mediated hydrolysis of bis(2,2,2-trifluoroethyl)-2,2-dimethylcyclopropane-1,1-dicarboxylate. Tetrahedron 2001, 57 (14), 2781-2786; (d) Debache, A.; Collet, S.; Bauchat, P.; Danion, D.; Euzenat, L.; Hercouet, A.; Carboni, B. Belokon's Ni(II) complex as a chiral masked glycine for the diastereoselective synthesis of 2-substituted 1-aminocyclo-propane carboxylic acids. Tetrahedron: Asymmetry 2001, 12 (5), 761-764; (e) Racouchot, S.; Ollivier, J.; Salaun, J. Titanium-mediated diastereoselective formation of (Z)-1-(1-alkenyl)-2-substituted-cyclopropyl esters efficient precursors of (Z)-2,3-methanoamino acids. Synlett 2000, 12, 1729-1732; (f) Abellan, T.; Chinchilla, R.; Galindo, N.; Najera, C.; Sansano, J.M. New oxazinone and pyrazinone derivatives as chiral reagents for the asymmetric synthesis of α-amino acids. J. Heterocyclic Chem. 2000, 37 (3), 467-479; (g) Katagiri, T.; Irie, M.; Minoru, U.K. Syntheses of optically active trifluoronorcoronamic acids. Org. Lett. 2000, 2 (16), 2423-2425; (h) Donkor, I.O.; Zheng, X.; Han, J.; Miller, D.D. Asymmetric synthesis of 2,3-methanoleucine stereoisomers from common intermediates. Chirality 2000, 12, 551-557; (i) Chinchilla, R.; Falvello, L.R.; Galindo, N.; Najera, C. New chiral didehydroamino acid derivatives from a cyclic glycine template with 3,6-dihydro-2H-1,4-oxazin-2-one structure: applications to the asymmetric synthesis of nonproteinogenic α-amino acids. J. Org. Chem. 2000, 65 (10), 3034-3041; (j) Kordes, M.; Winsel, H.; de Meijere, A. Cyclopropyl building blocks for organic synthesis 58; A new short access to amino acids incorporating an aminocyclopropyl moiety from N,N-dibenzyl-carboxamides. Eur. J. Org. Chem. 2000, 18, 3235-3245; (k) Kozyrkov, Y.; Pukin, A.; Kulinkovich, O.; Ollivier, J.; Salaun, J. A convenient approach to substituted 1-(1-alkenyl)cyclopropanols: a new preparation of 2,3-methano amino acids. Tetrahedron Lett. 2000, 41 (33), 6399-6402; (l) Dorizon, P.; Su, G.; Ludvig, G.; Nikitina, L.; Paugam, R.; Ollivier, J.; Salaun, J. Stereoselective synthesis of highly functionalized cyclopropanes. Application to the asymmetric synthesis of (1S,2S)-2,3-methanoamino acids. J. Org. Chem. 1999, 64 (13), 4712-4724.
28. For some selected recent examples about the synthesis of 2-substituted or 2,2-disubstituted ACCs, see: (a) Abellan, T.; Mancheno, B.; Najera, C.; Sansano, J.M. Asymmetric synthesis of α-amino acids from α,β-(Z)-didehydroamino acid derivatives with 1,2,3,6-tetra-hydropyrazin-2-one structure. Tetrahedron 2001, 57 (30), 6627-6640; (b) Clerici, F.; Gelmi, M.L.; Pocar, D.; Pilati, T. Masked constrained cysteines: diastereoselective and enantioselective synthesis of 1-amino-2-mercaptocyclo-propanecarboxylic acid derivatives. Tetrahedron: Asymmetry 2001, 12 (19), 2663-2669; (c) Salgado, A.; Huybrechts, T.; Eeckhaut, A.; Van der Eycken, J.; Szakonyi, Z.; Fulop, F.; Tkachev, A.; De Kimpe, N. Synthesis of (1S)-1-amino-2,2-dimethylcyclopropane-1-carboxylic acid via PLE mediated hydrolysis of bis(2,2,2-trifluoroethyl)-2,2-dimethylcyclopropane-1,1-dicarboxylate. Tetrahedron 2001, 57 (14), 2781-2786; (d) Debache, A.; Collet, S.; Bauchat, P.; Danion, D.; Euzenat, L.; Hercouet, A.; Carboni, B. Belokon's Ni(II) complex as a chiral masked glycine for the diastereoselective synthesis of 2-substituted 1-aminocyclo-propane carboxylic acids. Tetrahedron: Asymmetry 2001, 12 (5), 761-764; (e) Racouchot, S.; Ollivier, J.; Salaun, J. Titanium-mediated diastereoselective formation of (Z)-1-(1-alkenyl)-2-substituted-cyclopropyl esters efficient precursors of (Z)-2,3-methanoamino acids. Synlett 2000, 12, 1729-1732; (f) Abellan, T.;
29. For some selected recent examples about the synthesis of 2-substituted or 2,2-disubstituted ACCs, see: (a) Abellan, T.; Mancheno, B.; Najera, C.; Sansano, J.M. Asymmetric synthesis of α-amino acids from α,β-(Z)-didehydroamino acid derivatives with 1,2,3,6-tetra-hydropyrazin-2-one structure. Tetrahedron 2001, 57 (30), 6627-6640; (b) Clerici, F.; Gelmi, M.L.; Pocar, D.; Pilati, T. Masked constrained cysteines: diastereoselective and enantioselective synthesis of 1-amino-2-mercaptocyclo-propanecarboxylic acid derivatives. Tetrahedron: Asymmetry 2001, 12 (19), 2663-2669; (c) Salgado, A.; Huybrechts, T.; Eeckhaut, A.; Van der Eycken, J.; Szakonyi, Z.; Fulop, F.; Tkachev, A.; De Kimpe, N. Synthesis of (1S)-1-amino-2,2-dimethylcyclopropane-1-carboxylic acid via PLE mediated hydrolysis of bis(2,2,2-trifluoroethyl)-2,2-dimethylcyclopropane-1,1-dicarboxylate. Tetrahedron 2001, 57 (14), 2781-2786; (d) Debache, A.; Collet, S.; Bauchat, P.; Danion, D.; Euzenat, L.; Hercouet, A.; Carboni, B. Belokon's Ni(II) complex as a chiral masked glycine for the diastereoselective synthesis of 2-substituted 1-aminocyclo-propane carboxylic acids. Tetrahedron: Asymmetry 2001, 12 (5), 761-764; (e) Racouchot, S.; Ollivier, J.; Salaun, J. Titanium-mediated diastereoselective formation of (Z)-1-(1-alkenyl)-2-substituted-cyclopropyl esters efficient precursors of (Z)-2,3-methanoamino acids. Synlett 2000, 12, 1729-1732; (f) Abellan, T.; Chinchilla, R.; Galindo, N.; Najera, C.; Sansano, J.M. New oxazinone and pyrazinone derivatives as chiral reagents for the asymmetric synthesis of α-amino acids. J. Heterocyclic Chem. 2000, 37 (3), 467-479; (g) Katagiri, T.; Irie, M.; Minoru, U.K. Syntheses of optically active trifluoronorcoronamic acids. Org. Lett. 2000, 2 (16), 2423-2425; (h) Donkor, I.O.; Zheng, X.; Han, J.; Miller, D.D. Asymmetric synthesis of 2,3-methanoleucine stereoisomers from common intermediates. Chirality 2000, 12, 551-557; (i) Chinchilla, R.; Falvello, L.R.; Galindo, N.; Najera, C. New chiral didehydroamino acid derivatives from a cyclic glycine template with 3,6-dihydro-2H-1,4-oxazin-2-one structure: applications to the asymmetric synthesis of nonproteinogenic α-amino acids. J. Org. Chem. 2000, 65 (10), 3034-3041; (j) Kordes, M.; Winsel, H.; de Meijere, A. Cyclopropyl building blocks for organic synthesis 58; A new short access to amino acids incorporating an aminocyclopropyl moiety from N,N-dibenzyl-carboxamides. Eur. J. Org. Chem. 2000, 18, 3235-3245; (k) Kozyrkov, Y.; Pukin, A.; Kulinkovich, O.; Ollivier, J.; Salaun, J. A convenient approach to substituted 1-(1-alkenyl)cyclopropanols: a new preparation of 2,3-methano amino acids. Tetrahedron Lett. 2000, 41 (33), 6399-6402; (l) Dorizon, P.; Su, G.; Ludvig, G.; Nikitina, L.; Paugam, R.; Ollivier, J.; Salaun, J. Stereoselective synthesis of highly functionalized cyclopropanes. Application to the asymmetric synthesis of (1S,2S)-2,3-methanoamino acids. J. Org. Chem. 1999, 64 (13), 4712-4724.
30. For some selected recent examples about the synthesis of 2-substituted or 2,2-disubstituted ACCs, see: (a) Abellan, T.; Mancheno, B.; Najera, C.; Sansano, J.M. Asymmetric synthesis of α-amino acids from α,β-(Z)-didehydroamino acid derivatives with 1,2,3,6-tetra-hydropyrazin-2-one structure. Tetrahedron 2001, 57 (30), 6627-6640; (b) Clerici, F.; Gelmi, M.L.; Pocar, D.; Pilati, T. Masked constrained cysteines: diastereoselective and enantioselective synthesis of 1-amino-2-mercaptocyclo-propanecarboxylic acid derivatives. Tetrahedron: Asymmetry 2001, 12 (19), 2663-2669; (c) Salgado, A.; Huybrechts, T.; Eeckhaut, A.; Van der Eycken, J.; Szakonyi, Z.; Fulop, F.; Tkachev, A.; De Kimpe, N. Synthesis of (1S)-1-amino-2,2-dimethylcyclopropane-1-carboxylic acid via PLE mediated hydrolysis of bis(2,2,2-trifluoroethyl)-2,2-dimethylcyclopropane-1,1-dicarboxylate. Tetrahedron 2001, 57 (14), 2781-2786; (d) Debache, A.; Collet, S.; Bauchat, P.; Danion, D.; Euzenat, L.; Hercouet, A.; Carboni, B. Belokon's Ni(II) complex as a chiral masked glycine for the diastereoselective synthesis of 2-substituted 1-aminocyclo-propane carboxylic acids. Tetrahedron: Asymmetry 2001, 12 (5), 761-764; (e) Racouchot, S.; Ollivier, J.; Salaun, J. Titanium-mediated diastereoselective formation of (Z)-1-(1-alkenyl)-2-substituted-cyclopropyl esters efficient precursors of (Z)-2,3-methanoamino acids. Synlett 2000, 12, 1729-1732; (f) Abellan, T.; Chinchilla, R.; Galindo, N.; Najera, C.; Sansano, J.M. New oxazinone and pyrazinone derivatives as chiral reagents for the asymmetric synthesis of α-amino acids. J. Heterocyclic Chem. 2000, 37 (3), 467-479; (g) Katagiri, T.; Irie, M.; Minoru, U.K. Syntheses of optically active trifluoronorcoronamic acids. Org. Lett. 2000, 2 (16), 2423-2425; (h) Donkor, I.O.; Zheng, X.; Han, J.; Miller, D.D. Asymmetric synthesis of 2,3-methanoleucine stereoisomers from common intermediates. Chirality 2000, 12, 551-557; (i) Chinchilla, R.; Falvello, L.R.; Galindo, N.; Najera, C. New chiral didehydroamino acid derivatives from a cyclic glycine template with 3,6-dihydro-2H-1,4-oxazin-2-one structure: applications to the asymmetric synthesis of nonproteinogenic α-amino acids. J. Org. Chem. 2000, 65 (10), 3034-3041; (j) Kordes, M.; Winsel, H.; de Meijere, A. Cyclopropyl building blocks for organic synthesis 58; A new short access to amino acids incorporating an aminocyclopropyl moiety from N,N-dibenzyl-carboxamides. Eur. J. Org. Chem. 2000, 18, 3235-3245; (k) Kozyrkov, Y.; Pukin, A.; Kulinkovich, O.; Ollivier, J.; Salaun, J. A convenient approach to substituted 1-(1-alkenyl)cyclopropanols: a new preparation of 2,3-methano amino acids. Tetrahedron Lett. 2000, 41 (33), 6399-6402; (l) Dorizon, P.; Su, G.; Ludvig, G.; Nikitina, L.; Paugam, R.; Ollivier, J.; Salaun, J. Stereoselective synthesis of highly functionalized cyclopropanes. Application to the asymmetric synthesis of (1S,2S)-2,3-methanoamino acids. J. Org. Chem. 1999, 64 (13), 4712-4724.
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