Preparation of new chiral building blocks: Highly enantioselective reduction of prochiral 1,3-cycloalkanediones possessing a methyl group and a protected hydroxymethyl group at their C2 position with Baker's yeast or CBS catalyst

Hideaki Watanabe, Mitsuhiro Iwamoto, Masahisa Nakada*

*この研究の対応する著者

研究成果: Article査読

42 被引用数 (Scopus)

抄録

Highly enantioselective reduction of five-, six-, seven-, and eight-membered prochiral 1,3-cycloalkanediones possessing a methyl group and a protected hydroxymethyl group at their C2 position with baker's yeast or CBS catalyst and a new efficient and general method for preparing the 1,3-cycloalkanediones have been developed. These baker's yeast mediated reductions were found to produce corresponding ketols with high optical purity (> 99% ee) and high yield. All of the prepared ketols and their derivatives, chiral building blocks, have been fully characterized, and their absolute configurations have been determined. These compounds would be useful for the convergent synthesis of complex natural products.

本文言語English
ページ(範囲)4652-4658
ページ数7
ジャーナルJournal of Organic Chemistry
70
12
DOI
出版ステータスPublished - 2005 6月 12

ASJC Scopus subject areas

  • 有機化学

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