Enantioselective organocatalytic Michael addition of aldehydes to nitroethylene: efficient access to gamma2-amino acids.
Enantioselective organocatalytic Michael addition of aldehydes to nitroethylene catalyzed by (S)-diphenylprolinol silyl ether provides beta-substituted-delta-nitroalcohols in nearly optically pure form (96-99% ee). The Michael adducts bear a single substituent adjacent to the carbonyl and can be efficiently converted to protected gamma2-amino acids, which are essential for the systematic conformational studies of gamma-peptide foldamers.
Chi
Yonggui
Y
Department of Chemistry, University of Wisconsin, Madison, Wisconsin 53706, USA.
Guo
Li
L
Kopf
Nathan A
NA
Gellman
Samuel H
SH
D000438:Alcohols / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry*; D000596:Amino Acids / Q000138:chemical synthesis*; D002244:Carbon / Q000737:chemistry; D002384:Catalysis; D004987:Ethers / Q000737:chemistry; D005030:Ethylenes / Q000737:chemistry*; D008956:Models, Chemical; D009574:Nitro Compounds / Q000737:chemistry*; D017646:Organosilicon Compounds / Q000737:chemistry*; D011392:Proline / Q000737:chemistry; D013237:Stereoisomerism
D000438:Alcohols; D000447:Aldehydes; D000596:Amino Acids; D004987:Ethers; D005030:Ethylenes; D009574:Nitro Compounds; D017646:Organosilicon Compounds; D002244:Carbon; D011392:Proline