Article ID Journal Published Year Pages File Type
5224611 Tetrahedron 2010 10 Pages PDF
Abstract

The application of L-Selectride, either alone or in combination with ZnCl2, to aryl ketones 1, 8 and 11 resulted in highly anti-stereoselective reduction. In contrast, lactols 22 and 23 gave a moderate syn-preference using L-Selectride alone and a high syn-preference in the presence of ZnCl2. Uniquely, high anti- stereoselectivity was observed in the reduction of o-anisyl lactol 37 with L-Selectride alone, which was switched to a high syn-preference when ZnCl2 was present.

Graphical abstractThe influence of added ZnCl2 on the illustrated reductions is shown to be highly dependent on the nature of both the substrate (ketone or lactol) and the Ar group.Download full-size image

Related Topics
Physical Sciences and Engineering Chemistry Organic Chemistry
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