The Journal of Organic Chemistry

Lanthanides in organic synthesis. 4. Reduction of. alpha.,. beta.-epoxy ketones with samarium diiodide. A route to chiral, nonracemic aldols

GA Molander, G Hahn

Index: Molander, Gary A.; Hahn, Gregory Journal of Organic Chemistry, 1986 , vol. 51, # 13 p. 2596 - 2599

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Citation Number: 174

Abstract

We recently described reduction of a-heterosubstituted ketones to the corresponding unsubstituted ketones utilizing samarium diiodide (Sm12). l A variety of heterosubstituents can be reductively cleaved by this procedure under exceedingly mild conditions. Similar procedures applied to cy, P-epoxy ketones result in formation of 0-hydroxy ketones (aldols), of intense interest as key intermediates in construction of a variety of important natural ...

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