原创力文档diastereoselective desymmetrization of symmetric dienes and its synthetic applicationdiastereoselective desymmetrization对称双烯及其合成的应用程序.pdfVIP
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diastereoselective desymmetrization of symmetric dienes and its synthetic applicationdiastereoselective desymmetrization对称双烯及其合成的应用程序
Symmetry 2010, 2, 437-454; doi:10.3390/sym2020437
OPEN ACCESS
symmetry
ISSN 2073-8994
/journal/symmetry
Review
Diastereoselective Desymmetrization of Symmetric Dienes and
its Synthetic Application
Kenji Nakahara and Hiromichi Fujioka *
Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamada-oka, Suita, Osaka 565-
0871, Japan; E-Mail: ken512@phs.osaka-u.ac.jp
* Author to whom correspondence should be addressed; E-Mail: fujioka@phs.osaka-u.ac.jp
Received: 30 January 2010; in revised form: 4 March 2010 / Accepted: 4 March 2010 /
Published: 25 March 2010
Abstract: The desymmetrization of symmetric compounds is a useful approach to obtain
chiral building blocks. Readily available precursors with a prochiral unit could be converted
into complex molecules with multiple stereogenic centers in a single step. In this review,
recent advances in the desymmetrization of symmetric dienes in the diastereotopic group
differentiating reaction and its synthetic application are presented.
Keywords: desymmetrization; symmetric diene; chiral auxiliary; C -symmetric diol; acetal
2
1. Introduction
The desymmetrization of meso compounds has become one of the most powerful strategies in
organic synthesis [1]. It allows the formation of multiple chiral centers in a single step and offers an
entry to a wide range of stereochemically complex molecules including natural products. The main
advanta
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