Highly stereoselective Michael addition reactions of CamTHP*- desymmetrized glycinamide for the synthesis of functionally dense amino acid derivatives

Organic Letters

Volumn 6, Issue 24, 2004, Pages 4427-4429

  Dixon, Darren J ^a   Horan, Richard A J ^b   Monck, Nathaniel J T ^c   Berg, Paul ^b  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

^b UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^c Vernalis PLC   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; AMINO ACID DERIVATIVE; DIAMINO ACID; ESTER DERIVATIVE; GLYCINAMIDE; KETONE DERIVATIVE; LACTONE DERIVATIVE; LITHIUM DERIVATIVE; LITHIUM ENOLATE; PYROGLUTAMIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; DENSITY; DERIVATIZATION; ENANTIOMER; ENANTIOSELECTIVITY; MICHAEL ADDITION; MOLECULE; REACTION ANALYSIS; STEREOCHEMISTRY; SUBSTITUTION REACTION;

AMINO ACIDS; CAMPHOR; GLYCINE; STEREOISOMERISM;

EID: 10044294988     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048568q     Document Type: Article

References (18)

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5. (c) Hruby, V. J.; Sharma, S. D.; Collins, N.; Matsunaga, T. O.; Russell, K. C In Synthetic Peptides: A User's Guide; Grant, G. A., Ed.; W. H. Freeman and Co.: New York, 1992; p 259.
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7. (a) For a highly diastereoselective but racemic synthesis, see: Soloshonok, V. A.; Cai, C.; Hruby, V. J.; Van Meervelt, L.; Yamazaki, T. J. Org. Chem. 2000, 65, 6688.
8. For asymmetric examples, see: (b) Busch, K.; Groth, U. M.; Kühnle, W.; Schöllkopf, U. Tetrahedron 1992, 48, 5607. (c) Schöllkopf, U.; Kühnle, W.; Egert, E.; Dyrbusch, M. Angew. Chem., Int. Ed. Engl. 1987, 26, 480. (d) Pettig, D.; Schöllkopf, U.; Synthesis 1988, 173.
9. For asymmetric examples, see: (b) Busch, K.; Groth, U. M.; Kühnle, W.; Schöllkopf, U. Tetrahedron 1992, 48, 5607. (c) Schöllkopf, U.; Kühnle, W.; Egert, E.; Dyrbusch, M. Angew. Chem., Int. Ed. Engl. 1987, 26, 480. (d) Pettig, D.; Schöllkopf, U.; Synthesis 1988, 173.
10. For asymmetric examples, see: (b) Busch, K.; Groth, U. M.; Kühnle, W.; Schöllkopf, U. Tetrahedron 1992, 48, 5607. (c) Schöllkopf, U.; Kühnle, W.; Egert, E.; Dyrbusch, M. Angew. Chem., Int. Ed. Engl. 1987, 26, 480. (d) Pettig, D.; Schöllkopf, U.; Synthesis 1988, 173.
11. For an example using an achiral glycine anion and chiral electrophiles, see: (e) Soloshonok, V. A.; Ueki, H.; Tiwari, R.; Cai, C.; Hruby, V. J. J. Org. Chem. 2004, 69, 4984 and references therein.
12. Dixon, D. J.; Horan, R. A. J.; Monck, N. J. T. Org. Lett. 2004, 6, 4423.
13. Although an open transition-state model cannot be ruled out: Smitrovich, J. H.; DiMichele, L.; Qu, C.; Boice, G. N.; Nelson, T. D.; Huffman, M. A.; Murry, J. J. Org. Chem. 2004, 69, 1903.
14. For some excellent works on the steric course of enolate Michael addition reactions, see: (a) Suzuki, K.; Seebach, D. Liebigs Ann. Chem. 1992, 51. (b) Oare, D. A.; Henderson, M. A.; Sanner, M. A.; Heathcock, C. H. J. Org. Chem. 1990, 55, 132. (c) Oare, D. A.; Heathcock, C. H. J. Org. Chem. 1990, 55, 157.
15. For some excellent works on the steric course of enolate Michael addition reactions, see: (a) Suzuki, K.; Seebach, D. Liebigs Ann. Chem. 1992, 51. (b) Oare, D. A.; Henderson, M. A.; Sanner, M. A.; Heathcock, C. H. J. Org. Chem. 1990, 55, 132. (c) Oare, D. A.; Heathcock, C. H. J. Org. Chem. 1990, 55, 157.
16. For some excellent works on the steric course of enolate Michael addition reactions, see: (a) Suzuki, K.; Seebach, D. Liebigs Ann. Chem. 1992, 51. (b) Oare, D. A.; Henderson, M. A.; Sanner, M. A.; Heathcock, C. H. J. Org. Chem. 1990, 55, 132. (c) Oare, D. A.; Heathcock, C. H. J. Org. Chem. 1990, 55, 157.
17. The relative stereochemistry of 19 is supported by NOE (see the Supporting Information).
18. Adderley, N. J.; Buchanan, D. J.; Dixon, D. J.; Lainé, D. I. Angew. Chem., Int. Ed. 2003, 42, 4241.