Copper catalyzed asymmetric propargylation of aldehydes.
The highly enantio- and regioselective copper catalyzed asymmetric propargylation of aldehydes with a propargyl borolane reagent is reported. The methodology demonstrated broad functional group tolerance and provided high enantioselectivities for aliphatic, vinyl, and aryl aldehydes. The utility of the TMS homopropargylic alcohols was demonstrated by the facile conversion to a chiral dihydropyranone.
Fandrick
Daniel R
DR
Chemical Development, Boehringer Ingelheim Pharmaceuticals Inc., 900 Ridgebury Road/P.O. Box 368, Ridgefield, Connecticut 06877-0368, USA. daniel.fandrick@boehringer-ingelheim.com
Fandrick
Keith R
KR
Reeves
Jonathan T
JT
Tan
Zhulin
Z
Tang
Wenjun
W
Capacci
Andrew G
AG
Rodriguez
Sonia
S
Song
Jinhua J
JJ
Lee
Heewon
H
Yee
Nathan K
NK
Senanayake
Chris H
CH
D000447:Aldehydes / Q000737:chemistry*; D001896:Boron Compounds / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D000447:Aldehydes; D001896:Boron Compounds; D003300:Copper