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Catalytic Regio- and Enantioselective Haloazidation of Allylic Alcohols.

ABSTRACT: Herein we report a highly regio- and stereoselective haloazidation of allylic alcohols. This enantioselective reaction uses readily available materials and can be performed on a variety of alkyl-substituted alkenes and can incorporate either bromine or chlorine as the electrophilic halogen component. Both halide and azido groups of the resulting products can be transformed into valuable building blocks with complete stereospecificity. The first example of an enantioselective 1,4-haloazidation of a conjugated diene is reported as well as its application to a concise synthesis of an aza-sugar.

SUBMITTER: Seidl FJ

PROVIDER: S-EPMC6499076 | biostudies-literature | 2018 Nov

REPOSITORIES: biostudies-literature

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Catalytic Regio- and Enantioselective Haloazidation of Allylic Alcohols.

Seidl Frederick J FJ Min Chang C Lopez Jovan A JA Burns Noah Z NZ

Journal of the American Chemical Society 20181112 46

Herein we report a highly regio- and stereoselective haloazidation of allylic alcohols. This enantioselective reaction uses readily available materials and can be performed on a variety of alkyl-substituted alkenes and can incorporate either bromine or chlorine as the electrophilic halogen component. Both halide and azido groups of the resulting products can be transformed into valuable building blocks with complete stereospecificity. The first example of an enantioselective 1,4-haloazidation of ...[more]

PMID: 30403852

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