Highly (E)-selective BF(3).Et(2)O-promoted allylboration of chiral nonracemic alpha-substituted allylboronates and analysis of the origin of stereocontrol

Academic Article
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publication date

  • June 2010

abstract

  • Delta-methyl-substituted homoallylic alcohols 2 were prepared in 71-88% yield, E:Z >30:1 and 93% to >95% ee via BF(3).Et(2)O-promoted allylboration with alpha-Me-allylboronate 1. The origin of high (E)-selectivity is proposed.