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Abstract ( Z )‐2‐Butenyl‐dimethoxyborane adds smoothly to propanal and benzaldehyde to afford the homoallyl alcohols ( R *, R *)‐ 1 and ( R *, R *)‐ 2 , In contrast ( E )‐2‐butenyl‐dimethoxyborane leads to adducts having the ( R *, S *)‐configuration. Dimethoxy‐( Z )‐2‐pentenylborane, dimethoxy‐( Z )‐(2‐methyl‐2‐butenyl)borane and (2 Z ,4 E )‐or (2 E ,4 Z )hexadienyl‐dimethoxyborane, treated with propanal, give ( R *, R *)‐ 3 , ( R *, R *)‐ 4 , ( E ),( R *, S *)‐ 5 and ( Z ),( R *, R *)‐ 5 , respectively. A transition state model implying a pericyclic electron motion is in perfect agreement with the regio‐ and stereoselective outcome of these borane reactions.
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Fujitta et al. (1982) studied this question.
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