Tandem asymmetric allylboration–alkene metathesis: a novel strategy for the synthesis of trans-disubstituted homoallylic alcohols

AGM Barrett, JC Beall, VC Gibson, MR Giles…

Index: Barrett, Anthony G. M.; Beall, Jennifer C.; Gibson, Vernon C.; Giles, Matthew R.; Walker, Gary L. P. Chemical Communications, 1996 , # 19 p. 2229 - 2230

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Abstract

Tandem use of Brown's asymmetric allylboration technol- ogy and crossed-alkene metathesis provides exclusively trans-disubstituted homoallylic alcohols in good yields. ... The condensation reaction of allylborane reagents with alde- hydes represents a strategy of considerable merit in asymmetric synthesis (Scheme 1). The reaction of an aldehyde 1 with an allylborane 2 proceeds via a 6-centre chair transition state to provide the adduct 3 and subsequently the ...