5-Spirocyclopropane isoxazolidines as versatile intermediates in organic synthesis

Monatshefte fur Chemie

Volumn 135, Issue 6, 2004, Pages 649-669

  Cordero, Franca M ^a   De Sarlo, Francesco ^a   Brandi, Alberto ^a  

^a UNIVERSITY OF FLORENCE   (Italy)

Author keywords

Nitrogen heterocycles; Ring contraction; Ring expansion; Small ring system; Thermal rearrangement

Indexed keywords

ISOXAZOLIDINE DERIVATIVE;

AMNION BAND; CHEMICAL REACTION; CONFERENCE PAPER; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 2942568420     PISSN: 00269247     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00706-003-0150-x     Document Type: Conference Paper

References (54)

1. For some reviews see: a) Tufariello JJ (1984) Nitrones. In: Padwa A (ed) 1,3-Dipolar Cycloaddition Chemistry, vol 2. Wiley, New York, p 83-168; b) Torssell KBG (1988) Nitrile oxides, Nitrones and Nitronates in Organic Synthesis. VCH, New York; c) Confalone PN, Huie EM (1988) Org React 36: 1-173; d) Breuer E, Aurich HG, Nielsen A (1989) Nitrones, Nitronates, and Nitroxides. Wiley, New York, p 139-312; e) Padwa A (1991) In: Trost BM (ed) Comprehensive Organic Synthesis, Pergamon, Oxford, p 1069-1109; f) Frederickson M (1997) Tetrahedron 53: 403-425; g) Gothelf KV, Jørgensen KA (1998) Chem Rev 98: 863-909; h) Gothelf KV, Jørgensen KA (2000) Chem Commun 1449-1458; i) Karlsson S, Hogberg HE (2001) Org Prep Proced Int 33: 103-172; j) Osborn HMI, Gemmell N, Harwood LM (2002) J Chem Soc, Perkin Trans 1 2419-2438; k) Kanemasa S (2002) Synlett 9: 1371-1387; l) Bates RW, Sa-Ei K (2002) Tetrahedron 58: 5957-5978; m) Gallos JK, Koumbis AE (2003) Curr Org Chem 7: 397-425
2. For some reviews see: a) Tufariello JJ (1984) Nitrones. In: Padwa A (ed) 1,3-Dipolar Cycloaddition Chemistry, vol 2. Wiley, New York, p 83-168; b) Torssell KBG (1988) Nitrile oxides, Nitrones and Nitronates in Organic Synthesis. VCH, New York; c) Confalone PN, Huie EM (1988) Org React 36: 1-173; d) Breuer E, Aurich HG, Nielsen A (1989) Nitrones, Nitronates, and Nitroxides. Wiley, New York, p 139-312; e) Padwa A (1991) In: Trost BM (ed) Comprehensive Organic Synthesis, Pergamon, Oxford, p 1069-1109; f) Frederickson M (1997) Tetrahedron 53: 403-425; g) Gothelf KV, Jørgensen KA (1998) Chem Rev 98: 863-909; h) Gothelf KV, Jørgensen KA (2000) Chem Commun 1449-1458; i) Karlsson S, Hogberg HE (2001) Org Prep Proced Int 33: 103-172; j) Osborn HMI, Gemmell N, Harwood LM (2002) J Chem Soc, Perkin Trans 1 2419-2438; k) Kanemasa S (2002) Synlett 9: 1371-1387; l) Bates RW, Sa-Ei K (2002) Tetrahedron 58: 5957-5978; m) Gallos JK, Koumbis AE (2003) Curr Org Chem 7: 397-425
3. For some reviews see: a) Tufariello JJ (1984) Nitrones. In: Padwa A (ed) 1,3-Dipolar Cycloaddition Chemistry, vol 2. Wiley, New York, p 83-168; b) Torssell KBG (1988) Nitrile oxides, Nitrones and Nitronates in Organic Synthesis. VCH, New York; c) Confalone PN, Huie EM (1988) Org React 36: 1-173; d) Breuer E, Aurich HG, Nielsen A (1989) Nitrones, Nitronates, and Nitroxides. Wiley, New York, p 139-312; e) Padwa A (1991) In: Trost BM (ed) Comprehensive Organic Synthesis, Pergamon, Oxford, p 1069-1109; f) Frederickson M (1997) Tetrahedron 53: 403-425; g) Gothelf KV, Jørgensen KA (1998) Chem Rev 98: 863-909; h) Gothelf KV, Jørgensen KA (2000) Chem Commun 1449-1458; i) Karlsson S, Hogberg HE (2001) Org Prep Proced Int 33: 103-172; j) Osborn HMI, Gemmell N, Harwood LM (2002) J Chem Soc, Perkin Trans 1 2419-2438; k) Kanemasa S (2002) Synlett 9: 1371-1387; l) Bates RW, Sa-Ei K (2002) Tetrahedron 58: 5957-5978; m) Gallos JK, Koumbis AE (2003) Curr Org Chem 7: 397-425
4. For some reviews see: a) Tufariello JJ (1984) Nitrones. In: Padwa A (ed) 1,3-Dipolar Cycloaddition Chemistry, vol 2. Wiley, New York, p 83-168; b) Torssell KBG (1988) Nitrile oxides, Nitrones and Nitronates in Organic Synthesis. VCH, New York; c) Confalone PN, Huie EM (1988) Org React 36: 1-173; d) Breuer E, Aurich HG, Nielsen A (1989) Nitrones, Nitronates, and Nitroxides. Wiley, New York, p 139-312; e) Padwa A (1991) In: Trost BM (ed) Comprehensive Organic Synthesis, Pergamon, Oxford, p 1069-1109; f) Frederickson M (1997) Tetrahedron 53: 403-425; g) Gothelf KV, Jørgensen KA (1998) Chem Rev 98: 863-909; h) Gothelf KV, Jørgensen KA (2000) Chem Commun 1449-1458; i) Karlsson S, Hogberg HE (2001) Org Prep Proced Int 33: 103-172; j) Osborn HMI, Gemmell N, Harwood LM (2002) J Chem Soc, Perkin Trans 1 2419-2438; k) Kanemasa S (2002) Synlett 9: 1371-1387; l) Bates RW, Sa-Ei K (2002) Tetrahedron 58: 5957-5978; m) Gallos JK, Koumbis AE (2003) Curr Org Chem 7: 397-425
5. For some reviews see: a) Tufariello JJ (1984) Nitrones. In: Padwa A (ed) 1,3-Dipolar Cycloaddition Chemistry, vol 2. Wiley, New York, p 83-168; b) Torssell KBG (1988) Nitrile oxides, Nitrones and Nitronates in Organic Synthesis. VCH, New York; c) Confalone PN, Huie EM (1988) Org React 36: 1-173; d) Breuer E, Aurich HG, Nielsen A (1989) Nitrones, Nitronates, and Nitroxides. Wiley, New York, p 139-312; e) Padwa A (1991) In: Trost BM (ed) Comprehensive Organic Synthesis, Pergamon, Oxford, p 1069-1109; f) Frederickson M (1997) Tetrahedron 53: 403-425; g) Gothelf KV, Jørgensen KA (1998) Chem Rev 98: 863-909; h) Gothelf KV, Jørgensen KA (2000) Chem Commun 1449-1458; i) Karlsson S, Hogberg HE (2001) Org Prep Proced Int 33: 103-172; j) Osborn HMI, Gemmell N, Harwood LM (2002) J Chem Soc, Perkin Trans 1 2419-2438; k) Kanemasa S (2002) Synlett 9: 1371-1387; l) Bates RW, Sa-Ei K (2002) Tetrahedron 58: 5957-5978; m) Gallos JK, Koumbis AE (2003) Curr Org Chem 7: 397-425
6. For some reviews see: a) Tufariello JJ (1984) Nitrones. In: Padwa A (ed) 1,3-Dipolar Cycloaddition Chemistry, vol 2. Wiley, New York, p 83-168; b) Torssell KBG (1988) Nitrile oxides, Nitrones and Nitronates in Organic Synthesis. VCH, New York; c) Confalone PN, Huie EM (1988) Org React 36: 1-173; d) Breuer E, Aurich HG, Nielsen A (1989) Nitrones, Nitronates, and Nitroxides. Wiley, New York, p 139-312; e) Padwa A (1991) In: Trost BM (ed) Comprehensive Organic Synthesis, Pergamon, Oxford, p 1069-1109; f) Frederickson M (1997) Tetrahedron 53: 403-425; g) Gothelf KV, Jørgensen KA (1998) Chem Rev 98: 863-909; h) Gothelf KV, Jørgensen KA (2000) Chem Commun 1449-1458; i) Karlsson S, Hogberg HE (2001) Org Prep Proced Int 33: 103-172; j) Osborn HMI, Gemmell N, Harwood LM (2002) J Chem Soc, Perkin Trans 1 2419-2438; k) Kanemasa S (2002) Synlett 9: 1371-1387; l) Bates RW, Sa-Ei K (2002) Tetrahedron 58: 5957-5978; m) Gallos JK, Koumbis AE (2003) Curr Org Chem 7: 397-425
7. For some reviews see: a) Tufariello JJ (1984) Nitrones. In: Padwa A (ed) 1,3-Dipolar Cycloaddition Chemistry, vol 2. Wiley, New York, p 83-168; b) Torssell KBG (1988) Nitrile oxides, Nitrones and Nitronates in Organic Synthesis. VCH, New York; c) Confalone PN, Huie EM (1988) Org React 36: 1-173; d) Breuer E, Aurich HG, Nielsen A (1989) Nitrones, Nitronates, and Nitroxides. Wiley, New York, p 139-312; e) Padwa A (1991) In: Trost BM (ed) Comprehensive Organic Synthesis, Pergamon, Oxford, p 1069-1109; f) Frederickson M (1997) Tetrahedron 53: 403-425; g) Gothelf KV, Jørgensen KA (1998) Chem Rev 98: 863-909; h) Gothelf KV, Jørgensen KA (2000) Chem Commun 1449-1458; i) Karlsson S, Hogberg HE (2001) Org Prep Proced Int 33: 103-172; j) Osborn HMI, Gemmell N, Harwood LM (2002) J Chem Soc, Perkin Trans 1 2419-2438; k) Kanemasa S (2002) Synlett 9: 1371-1387; l) Bates RW, Sa-Ei K (2002) Tetrahedron 58: 5957-5978; m) Gallos JK, Koumbis AE (2003) Curr Org Chem 7: 397-425
8. For some reviews see: a) Tufariello JJ (1984) Nitrones. In: Padwa A (ed) 1,3-Dipolar Cycloaddition Chemistry, vol 2. Wiley, New York, p 83-168; b) Torssell KBG (1988) Nitrile oxides, Nitrones and Nitronates in Organic Synthesis. VCH, New York; c) Confalone PN, Huie EM (1988) Org React 36: 1-173; d) Breuer E, Aurich HG, Nielsen A (1989) Nitrones, Nitronates, and Nitroxides. Wiley, New York, p 139-312; e) Padwa A (1991) In: Trost BM (ed) Comprehensive Organic Synthesis, Pergamon, Oxford, p 1069-1109; f) Frederickson M (1997) Tetrahedron 53: 403-425; g) Gothelf KV, Jørgensen KA (1998) Chem Rev 98: 863-909; h) Gothelf KV, Jørgensen KA (2000) Chem Commun 1449-1458; i) Karlsson S, Hogberg HE (2001) Org Prep Proced Int 33: 103-172; j) Osborn HMI, Gemmell N, Harwood LM (2002) J Chem Soc, Perkin Trans 1 2419-2438; k) Kanemasa S (2002) Synlett 9: 1371-1387; l) Bates RW, Sa-Ei K (2002) Tetrahedron 58: 5957-5978; m) Gallos JK, Koumbis AE (2003) Curr Org Chem 7: 397-425
9. For some reviews see: a) Tufariello JJ (1984) Nitrones. In: Padwa A (ed) 1,3-Dipolar Cycloaddition Chemistry, vol 2. Wiley, New York, p 83-168; b) Torssell KBG (1988) Nitrile oxides, Nitrones and Nitronates in Organic Synthesis. VCH, New York; c) Confalone PN, Huie EM (1988) Org React 36: 1-173; d) Breuer E, Aurich HG, Nielsen A (1989) Nitrones, Nitronates, and Nitroxides. Wiley, New York, p 139-312; e) Padwa A (1991) In: Trost BM (ed) Comprehensive Organic Synthesis, Pergamon, Oxford, p 1069-1109; f) Frederickson M (1997) Tetrahedron 53: 403-425; g) Gothelf KV, Jørgensen KA (1998) Chem Rev 98: 863-909; h) Gothelf KV, Jørgensen KA (2000) Chem Commun 1449-1458; i) Karlsson S, Hogberg HE (2001) Org Prep Proced Int 33: 103-172; j) Osborn HMI, Gemmell N, Harwood LM (2002) J Chem Soc, Perkin Trans 1 2419-2438; k) Kanemasa S (2002) Synlett 9: 1371-1387; l) Bates RW, Sa-Ei K (2002) Tetrahedron 58: 5957-5978; m) Gallos JK, Koumbis AE (2003) Curr Org Chem 7: 397-425
10. For some reviews see: a) Tufariello JJ (1984) Nitrones. In: Padwa A (ed) 1,3-Dipolar Cycloaddition Chemistry, vol 2. Wiley, New York, p 83-168; b) Torssell KBG (1988) Nitrile oxides, Nitrones and Nitronates in Organic Synthesis. VCH, New York; c) Confalone PN, Huie EM (1988) Org React 36: 1-173; d) Breuer E, Aurich HG, Nielsen A (1989) Nitrones, Nitronates, and Nitroxides. Wiley, New York, p 139-312; e) Padwa A (1991) In: Trost BM (ed) Comprehensive Organic Synthesis, Pergamon, Oxford, p 1069-1109; f) Frederickson M (1997) Tetrahedron 53: 403-425; g) Gothelf KV, Jørgensen KA (1998) Chem Rev 98: 863-909; h) Gothelf KV, Jørgensen KA (2000) Chem Commun 1449-1458; i) Karlsson S, Hogberg HE (2001) Org Prep Proced Int 33: 103-172; j) Osborn HMI, Gemmell N, Harwood LM (2002) J Chem Soc, Perkin Trans 1 2419-2438; k) Kanemasa S (2002) Synlett 9: 1371-1387; l) Bates RW, Sa-Ei K (2002) Tetrahedron 58: 5957-5978; m) Gallos JK, Koumbis AE (2003) Curr Org Chem 7: 397-425
11. For some reviews see: a) Tufariello JJ (1984) Nitrones. In: Padwa A (ed) 1,3-Dipolar Cycloaddition Chemistry, vol 2. Wiley, New York, p 83-168; b) Torssell KBG (1988) Nitrile oxides, Nitrones and Nitronates in Organic Synthesis. VCH, New York; c) Confalone PN, Huie EM (1988) Org React 36: 1-173; d) Breuer E, Aurich HG, Nielsen A (1989) Nitrones, Nitronates, and Nitroxides. Wiley, New York, p 139-312; e) Padwa A (1991) In: Trost BM (ed) Comprehensive Organic Synthesis, Pergamon, Oxford, p 1069-1109; f) Frederickson M (1997) Tetrahedron 53: 403-425; g) Gothelf KV, Jørgensen KA (1998) Chem Rev 98: 863-909; h) Gothelf KV, Jørgensen KA (2000) Chem Commun 1449-1458; i) Karlsson S, Hogberg HE (2001) Org Prep Proced Int 33: 103-172; j) Osborn HMI, Gemmell N, Harwood LM (2002) J Chem Soc, Perkin Trans 1 2419-2438; k) Kanemasa S (2002) Synlett 9: 1371-1387; l) Bates RW, Sa-Ei K (2002) Tetrahedron 58: 5957-5978; m) Gallos JK, Koumbis AE (2003) Curr Org Chem 7: 397-425
12. For some reviews see: a) Tufariello JJ (1984) Nitrones. In: Padwa A (ed) 1,3-Dipolar Cycloaddition Chemistry, vol 2. Wiley, New York, p 83-168; b) Torssell KBG (1988) Nitrile oxides, Nitrones and Nitronates in Organic Synthesis. VCH, New York; c) Confalone PN, Huie EM (1988) Org React 36: 1-173; d) Breuer E, Aurich HG, Nielsen A (1989) Nitrones, Nitronates, and Nitroxides. Wiley, New York, p 139-312; e) Padwa A (1991) In: Trost BM (ed) Comprehensive Organic Synthesis, Pergamon, Oxford, p 1069-1109; f) Frederickson M (1997) Tetrahedron 53: 403-425; g) Gothelf KV, Jørgensen KA (1998) Chem Rev 98: 863-909; h) Gothelf KV, Jørgensen KA (2000) Chem Commun 1449-1458; i) Karlsson S, Hogberg HE (2001) Org Prep Proced Int 33: 103-172; j) Osborn HMI, Gemmell N, Harwood LM (2002) J Chem Soc, Perkin Trans 1 2419-2438; k) Kanemasa S (2002) Synlett 9: 1371-1387; l) Bates RW, Sa-Ei K (2002) Tetrahedron 58: 5957-5978; m) Gallos JK, Koumbis AE (2003) Curr Org Chem 7: 397-425
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