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Highly diastereoselective Pd-catalyzed carboetherification reactions of acyclic internal alkenes. Stereoselective synthesis of polysubstituted tetrahydrofurans.

ABSTRACT: A highly diastereoselective synthesis of substituted tetrahydrofurans bearing stereocenters at C2 and C1' via Pd-catalyzed carboetherification reactions of acyclic internal alkenes is described. Use of an improved catalyst composed of Pd(2)(dba)(3)/S-Phos provides products with up to >20:1 dr. The stereoselective preparation of tetrahydrofurans containing three stereocenters, including a molecule structurally related to simplakidine A, is also reported.

SUBMITTER: Ward AF

PROVIDER: S-EPMC2837786 | biostudies-literature | 2010 Mar

REPOSITORIES: biostudies-literature

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Highly diastereoselective Pd-catalyzed carboetherification reactions of acyclic internal alkenes. Stereoselective synthesis of polysubstituted tetrahydrofurans.

Ward Amanda F AF Wolfe John P JP

Organic letters 20100301 6

A highly diastereoselective synthesis of substituted tetrahydrofurans bearing stereocenters at C2 and C1' via Pd-catalyzed carboetherification reactions of acyclic internal alkenes is described. Use of an improved catalyst composed of Pd(2)(dba)(3)/S-Phos provides products with up to >20:1 dr. The stereoselective preparation of tetrahydrofurans containing three stereocenters, including a molecule structurally related to simplakidine A, is also reported. ...[more]

PMID: 20170146

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