Kinetic Resolution of 5-Substituted Cyclohexenols by Palladium-Catalyzed Asymmetric Redox-Relay Heck Reaction

The kinetic resolution of 2-substituted-cyclohexenols via palladium-catalyzed asymmetric redox-relay Heck reaction was realized, providing optically active 2-substituted cyclohexenols and trans-3,5-disubstituted cyclohexan-1-ones in high yield and good enantioselectivities with an S factor up to 22.

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Bibliographic Details
Published inSynthesis (Stuttgart) Vol. 49; no. 1; pp. 159 - 166
Main Authors Li, Hao, Gao, Ang, Liu, Xiu-Yan, Ding, Chang-Hua, Xu, Bin, Hou, Xue-Long
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 03.01.2017
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ALKENYL ALCOHOLS
ARYLATIONS
ALKYLATION
STRATEGY
Heck reaction
QUATERNARY STEREOCENTERS
ACYCLIC ALKENES
REGIOSELECTIVITY
cyclohexenol
P,N-LIGANDS
LIGANDS
cyclohexanone
ALLYLIC ALCOHOLS
kinetic resolution
palladium
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Summary:The kinetic resolution of 2-substituted-cyclohexenols via palladium-catalyzed asymmetric redox-relay Heck reaction was realized, providing optically active 2-substituted cyclohexenols and trans-3,5-disubstituted cyclohexan-1-ones in high yield and good enantioselectivities with an S factor up to 22.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0035-1562620