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Enantioselective redox-relay oxidative heck arylations of acyclic alkenyl alcohols using boronic acids.

ABSTRACT: A general, highly selective asymmetric redox-relay oxidative Heck reaction using achiral or racemic acyclic alkenols and boronic acid derivatives is reported. This reaction delivers remotely functionalized arylated carbonyl products from acyclic alkenol substrates, with excellent enantioselectivity under mild conditions, bearing a range of useful functionality. A preliminary mechanistic investigation suggests that the regioselectivity of the initial migratory insertion is highly dependent on the electronic nature of the boronic acid and more subtle electronic effects of the alkenyl alcohol.

SUBMITTER: Mei TS

PROVIDER: S-EPMC3698857 | biostudies-literature | 2013 May

REPOSITORIES: biostudies-literature

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Enantioselective redox-relay oxidative heck arylations of acyclic alkenyl alcohols using boronic acids.

Mei Tian-Sheng TS Werner Erik W EW Burckle Alexander J AJ Sigman Matthew S MS

Journal of the American Chemical Society 20130424 18

A general, highly selective asymmetric redox-relay oxidative Heck reaction using achiral or racemic acyclic alkenols and boronic acid derivatives is reported. This reaction delivers remotely functionalized arylated carbonyl products from acyclic alkenol substrates, with excellent enantioselectivity under mild conditions, bearing a range of useful functionality. A preliminary mechanistic investigation suggests that the regioselectivity of the initial migratory insertion is highly dependent on the ...[more]

PMID: 23607624

Similar Datasets

Enantioselective Heck arylations of acyclic alkenyl alcohols using a redox-relay strategy.

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