Asymmetric allylboration of alpha,beta-enals as a surrogate for the enantioselective synthesis of allylic amines and alpha-amino acids.
[reaction: see text] Optically pure allylic amines have been synthesized from alpha,beta-unsaturated aldehydes via allylboration with (-)-B-allyldiisopinocampheylborane, followed by Overman rearrangement. By incorporating crotyl and alkoxyallylboration, functionalization at delta-position was readily accomplished. By applying this methodology, the synthesis of several chiral alpha-amino acids has been achieved.
Ramachandran
P Veeraraghavan
PV
Herbert C. Brown Center for Borane Research, Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907-2084, USA chandran@purdue.edu
Burghardt
Thomas E
TE
Reddy
M Venkat Ram
MV
D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry; D000498:Allyl Compounds / Q000737:chemistry*; D000588:Amines / Q000138:chemical synthesis*; D000596:Amino Acids / Q000138:chemical synthesis*; D001896:Boron Compounds / Q000737:chemistry*; D008968:Molecular Conformation; D013237:Stereoisomerism
D000447:Aldehydes; D000498:Allyl Compounds; D000588:Amines; D000596:Amino Acids; D001896:Boron Compounds