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Stereoselective Synthesis of Alcohols, XLIV. Cyclization of Benzyloxy‐substituted (8‐Oxo‐2‐octenyl)boronates
Author(s) -
Sander Thomas,
Hoffmann Reinhard W.
Publication year - 1993
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.1993199301193
Subject(s) - chemistry , stereoselectivity , organic chemistry , medicinal chemistry , catalysis
The cyclization of (8‐oxo‐2‐octenyl)boronates having benzyloxy substituents in the chain linking the two functional groups gives benzyloxy‐substituted 2‐vinylcyclohexanols. High asymmetric induction is found for the 4‐ or 6‐benzyloxy‐( Z )‐octenylboronates 12a and 12c , whereas cyclization of the other isomers studied proceeded in a stereorandom fashion. Possible reasons for this unexpected behavior are discussed.