Volume 32, Issue 18
Preparative Organic Chemistry
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ChemInform Abstract: Stereoselective Synthesis of Secondary Organozinc Reagents and Their Reaction with Heteroatomic Electrophiles.

Eike Hupe

Eike Hupe

Inst. Org. Chem., Ludwig-Maximilians-Univ., D-81377 Muenchen, Germany

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Paul Knochel

Paul Knochel

Inst. Org. Chem., Ludwig-Maximilians-Univ., D-81377 Muenchen, Germany

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First published: 27 May 2010

Abstract

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ChemInform Abstract

Cyclic and acyclic trisubstituted alkenes are transformed to stable trans-configured diorganozinc reagents, which smoothly undergo reaction with various heteroatomic electrophiles to furnish tin-, sulfur-, or bromine-containing adducts in moderate yields and with retention of configuration. The utility of the method is demonstrated in the preparation of a chiral bisphosphine ligand (X) by enantioselective introduction of a phosphine oxide substituent into cyclic olefin (VII).

chemical structure image

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