Asymmetric Epoxidation of Homoallylic Alcohols and Application in a Concise Total Synthesis of (−)‐α‐Bisabolol and (−)‐8‐ epi ‐α‐Bisabolol | Zendy

Makita Naoya | Zendy; Hoshino Yujiro | Zendy; Yamamoto Hisashi | Zendy

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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.

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