Cobalt-Catalyzed Desymmetric Isomerization of Exocyclic Olefins

Chiral cyclic olefins, 1-methylcyclohexenes, are versatile building blocks for the synthesis of pharmaceuticals and natural products. Despite the prevalence of these structural motifs, the development of efficient synthetic methods remains an unmet challenge. Herein we report a novel desymmetric iso...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 143; no. 49; pp. 20633 - 20639
Main Authors Liu, Xufang, Rong, Xianle, Liu, Shihan, Lan, Yu, Liu, Qiang
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 15.12.2021
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
DOUBLE-BOND ISOMERIZATION
PRIMARY ALLYLIC ALCOHOLS
ALKENES
DIELS-ALDER
MONOISOMERIZATION
ASYMMETRIC ISOMERIZATION
MECHANISM
CHIRAL ALDEHYDES
ENANTIOSELECTIVE ISOMERIZATION
STRUCTURE ELUCIDATION
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Summary:Chiral cyclic olefins, 1-methylcyclohexenes, are versatile building blocks for the synthesis of pharmaceuticals and natural products. Despite the prevalence of these structural motifs, the development of efficient synthetic methods remains an unmet challenge. Herein we report a novel desymmetric isomerization of exocyclic olefins using a series of newly designed chiral cobalt catalysts, which enables a straightforward construction of chiral 1-methylcyclohexenes with diversified functionalities. The synthetic utility of this methodology is highlighted by a concise and enantioselective synthesis of a natural product, β-bisabolene. The versatility of the reaction products is further demonstrated by multifarious derivatizations.
Bibliography:ObjectType-Article-1
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ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.1c11343