One-pot enantioselective synthesis of optically active homoallylic alcohols from allyl halides.
A one-pot, convenient method for the preparation of optically active homoallylic alcohols from allyl halides was developed. Allyltrichlorosilanes were generated in situ from allyl halides and trichlorosilane in the presence of cuprous chloride and tertiary amine. Without isolation of the allyltrichlorosilanes, benzaldehyde and chiral biquinoline N,N'-dioxide were introduced into the same flask, producing the corresponding homoallylic alcohols with good to high enantioselectivities.
Nakajima
M
M
Graduate School of Pharmaceutical Sciences, Hokkaido University, Sapporo, Japan.
Saito
M
M
Hashimoto
S
S
D000438:Alcohols / Q000138:chemical synthesis*; D000498:Allyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D003300:Copper; D006219:Halogens; D012821:Silanes; D013237:Stereoisomerism
D000438:Alcohols; D000498:Allyl Compounds; D006219:Halogens; D012821:Silanes; D003300:Copper; C029892:cupric chloride