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An efficient 1,2-chelation-controlled reduction of protected hydroxy ketones via Red-Al.

Authors
  • Bajwa, Naval
  • Jennings, Michael P
Type
Published Article
Journal
The Journal of organic chemistry
Publication Date
May 02, 2008
Volume
73
Issue
9
Pages
3638–3641
Identifiers
DOI: 10.1021/jo800150x
PMID: 18357999
Source
Medline
License
Unknown

Abstract

In this paper, we have demonstrated that Red-Al is an efficient chelation-controlled reducing reagent for acyclic acetal (i.e., MOM, MEM, SEM, and BOM) protected alpha-hydroxy ketones. Typically, diastereomeric ratios (dr) ranged from 5 to 20:1 for the 1,2- anti-diols in good to excellent yields.

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