Chiral N-acyl-tert-butanesulfinamides: The 'safety-catch' principle applied to diastereoselective enolate alkylations

Journal of Organic Chemistry

Volumn 64, Issue 15, 1999, Pages 5472-5478

  Backes, Bradley J ^a   Dragoli, Dean R ^a   Ellman, Jonathan A ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

SULFINAMIDE;

ACYLATION; ALKYLATION; ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; DIASTEREOISOMER; OXIDATION; STEREOCHEMISTRY; STEREOSPECIFICITY; TEMPERATURE SENSITIVITY;

EID: 0033597843     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990271w     Document Type: Article

References (37)

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18. We have since employed tert-butanesulfinimines for the asymmetric synthesis of the following. (a) α-Substituted amines: Liu, G.; Cogan, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1997, 119, 9913. (b) α,α-Dibranched amines: Cogan, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1999, 121, 268. β-Substituted β-amino acids, β,β-disubstituted β-amino acids, and α,β-disubstituted β-amino acids: Tang, T. P.; Ellman, J. A. J. Org. Chem. 1999, 64, 12.
19. We have since employed tert-butanesulfinimines for the asymmetric synthesis of the following. (a) α-Substituted amines: Liu, G.; Cogan, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1997, 119, 9913. (b) α,α-Dibranched amines: Cogan, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1999, 121, 268. β-Substituted β-amino acids, β,β-disubstituted β-amino acids, and α,β-disubstituted β-amino acids: Tang, T. P.; Ellman, J. A. J. Org. Chem. 1999, 64, 12.
20. We have since employed tert-butanesulfinimines for the asymmetric synthesis of the following. (a) α-Substituted amines: Liu, G.; Cogan, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1997, 119, 9913. (b) α,α-Dibranched amines: Cogan, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1999, 121, 268. β-Substituted β-amino acids, β,β-disubstituted β-amino acids, and α,β-disubstituted β-amino acids: Tang, T. P.; Ellman, J. A. J. Org. Chem. 1999, 64, 12.
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