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Asymmetric Epoxidation of Homoallylic Alcohols and Application in a Concise Total Synthesis of (−)‐α‐Bisabolol and (−)‐8‐ epi ‐α‐Bisabolol
Author(s) -
Makita Naoya,
Hoshino Yujiro,
Yamamoto Hisashi
Publication year - 2003
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200390250
Subject(s) - catalysis , chemistry , organic chemistry , enantioselective synthesis , epoxy , hydroxamic acid , oxide
Vanadium triisopropoxide oxide and an α‐amino acid‐based hydroxamic acid (e.g. 1 ) form the catalyst for the asymmetric epoxidation of homoallylic alcohols presented here. 3‐Substituted alcohols 2 were epoxidized to the corresponding epoxy alcohols 3 with good ee values. In addition, a concise total synthesis of (−)‐α‐ and (−)‐8‐ epi ‐α‐bisabolol was achieved.