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Stereoselective synthesis of alcohols, XL. Stereoselective cyclization of 7-oxo-2-heptenylboronates

✍ Scribed by Hoffmann, Reinhard W. ;Niel, Gilles

Publisher
John Wiley and Sons
Year
1991
Tongue
English
Weight
681 KB
Volume
1991
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

Intramolecular allylboration reaction of 7‐oxo‐2‐heptenyl boronates leads to 2‐vinylcyclopentanols. The cyclization proceeds in a stereospecific manner, such that the (E)‐allylboronate 8 is converted into trans‐2‐vinylcyclopentanol (2) and the (Z)‐allylboronate 10 into cis‐2‐vinylcyclopentanol (3). Asymmetric induction originating from stereogenic centers placed between the boronate and the aldehyde function has been found to be low.

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