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ChemInform Abstract: Cuprous Chloride Accelerated Stille Reactions. A General and Effective Coupling System for Sterically Congested Substrates and for Enantioselective Synthesis.

โœ Scribed by Xiaojun Han; Brian M. Stoltz; E. J. Corey

Book ID
101892717
Publisher
John Wiley and Sons
Year
2010
Weight
35 KB
Volume
30
Category
Article
ISSN
0931-7597

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โœฆ Synopsis

Cuprous Chloride Accelerated Stille Reactions. A General and Effective Coupling System for Sterically Congested Substrates and for Enantioselective Synthesis.

-A new method is developed that utilizes CuCl/LiCl/Pd(0) for the coupling of aryl perfluoroalkanesulfonates, iodides, or bromides with 1-substituted vinyl stannanes to provide Stille products in excellent yields and without formation of cine substitution products, in contrast to low yields obtained by previously reported methods. The method is applied to the enantioselective synthesis of carbinol (VII), a model for the natural product nicandrenone.

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