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A convenient and diastereoselective route to homoallyl alcohols: Addition of (z)- or (e)-alkenyl-dimethoxyboranes to aldehydes

✍ Scribed by Katsuramaru Fujitta; Manfred Schloser

Publisher: John Wiley and Sons
Year: 1982
Tongue: German
Weight: 276 KB
Volume: 65
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19820650415

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✦ Synopsis

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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