Highly enantioselective mukaiyama aldol reactions catalyzed by a chiral oxazaborolidinium ion: total synthesis of (-)-inthomycin C.
A cationic oxazaborolidinium-catalyzed asymmetric Mukaiyama aldol reaction of (1-methoxy-2-methyl-propenyloxy)-trimethylsilane with various aldehydes including α,β-disubstituted acroleins has been developed in high yields and enantioselectivities. The synthetic utility of this methodology was demonstrated in the first short synthesis of naturally occurring inthomycin C in high enantiopurity.
Senapati
Bidyut Kumar
BK
Department of Chemistry, Sungkyunkwan University, Suwon, 440-746, Korea.
Gao
Lizhu
L
Lee
Sung Il
SI
Hwang
Geum-Sook
GS
Ryu
Do Hyun
DH
D000447:Aldehydes / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D001896:Boron Compounds / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D015394:Molecular Structure; D010080:Oxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D012821:Silanes / Q000737:chemistry; D013237:Stereoisomerism
D000447:Aldehydes; D001688:Biological Products; D001896:Boron Compounds; D010080:Oxazoles; D012821:Silanes; C554877:inthomycin C; C116609:3-hydroxybutanal