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Synthesis 2009(11): 1761-1785  
DOI: 10.1055/s-0029-1216818
REVIEW
© Georg Thieme Verlag Stuttgart ˙ New York

Transition-Metal-Catalyzed Enantioselective Synthesis of Compounds with Non-Centrochirality

Masamichi Ogasawara*, Susumu Watanabe
Catalysis Research Center and Graduate School of Life Science, Hokkaido University, Kita-ku, Sapporo 001-0021, Japan
Fax: +81(11)7069150; e-Mail: ogasawar@cat.hokudai.ac.jp;
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Publication History

Received 10 March 2009
Publication Date:
14 May 2009 (online)

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Transition-Metal-Catalyzed Enantioselective Synthesis of Compounds with Non-CentrochiralitySynthesis 2009; 2009(18): 3177-3178
DOI: 10.1055/s-0029-1216988

Abstract

Although central chirality based on stereogenic carbon atoms is arguably the most common chiral element in organic chemistry, chiral molecules devoid of stereogenic centers play important roles in stereoselective organic transformations. In spite of the usefulness of these chiral compounds with ‘non-centrochirality’ in asymmetric synthesis, enantiomerically enriched forms (scalemic forms) of these compounds are primarily obtained by rather classical methods. Examples of catalytic enantioselective induction of such non-centrochirality have been extremely rare and this is thus still a developing area in synthetic organic chemistry. In this review article, transition-metal-catalyzed enantioselective preparations of various non-centrochiral compounds, which include compounds with planar, axial, or helical chirality, are surveyed.

1 Introduction

2 Planar Chirality in Organometallic and Organic Compounds

3 Axial Chirality in Allenes

4 Atropisomeric Axial Chirality in Biaryls

5 Atropisomeric Axial Chirality about Carbon-Nitrogen or Carbon-Carbon Single Bonds in Nonbiaryl Systems

6 Axial Chirality in Spiro Compounds

7 Helical Chirality in ortho-Fused Polycyclic Aromatic Compounds

8 Conclusions

Key words

catalytic asymmetric synthesis - enantioselective reaction - transition-metal catalyst - homogeneous catalysis - non-centrochirality