Volume 20, Issue 22
Preparative Organic Chemistry
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ChemInform Abstract: Applications of α-Alkoxyorganocuprate Reagents in the Regiospecific Synthesis of Cyclic Homoaldol Products.

R. J. LINDERMAN

R. J. LINDERMAN

Dep. Chem., N. C. State Univ., Raleigh, NC 27695, USA

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A. GODFREY

A. GODFREY

Dep. Chem., N. C. State Univ., Raleigh, NC 27695, USA

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K. HORNE

K. HORNE

Dep. Chem., N. C. State Univ., Raleigh, NC 27695, USA

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First published: May 30, 1989

Abstract

A general route for the preparation of ca. 20 cyclic homoaldol products such as (VII) is described via conjugate addition of sec. and tert. substituted α-alkoxyorganocuprates derived from the stannanes (IV) to the non-sterically demanding enones (V).

ChemInform Abstract

A general route for the preparation of ca. 20 cyclic homoaldol products such as (VII) is described via conjugate addition of sec. and tert. substituted α-alkoxyorganocuprates derived from the stannanes (IV) to the non-sterically demanding enones (V). Most of the products are obtained as diastereomeric mixtures. Sterically demanding enones are less reactive or completely unreactive.

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