Stereoselective 4-benzyloxybut-2-enylation of aldehydes via an allyl-transfer reaction using a chiral allyl donor.
[reaction: see text] A direct and highly stereoselective (E)-4-benzyloxybut-2-enylation of aldehydes was successfully carried out to give 5-benzyloxyhomoallylic alcohol (11) via an allyl-transfer reaction using a chiral allyl donor (10). The chiral allyl donor (10) was prepared by catalytic Sharpless asymmetric epoxidation of 3-methylbut-2-en-1-ol, followed by a stereospecific vinyl Grignard reaction of the epoxide in the presence of CuBr and selective benzylation of the primary alcohol of diol.
Shafi
Siddiqi M
SM
Department of Applied Chemistry, Okayama University of Science, Japan.
Chou
Jingyu
J
Kataoka
Kazuhide
K
Nokami
Junzo
J