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Synthesis 2010(16): 2679-2702  
DOI: 10.1055/s-0030-1258164
REVIEW
© Georg Thieme Verlag Stuttgart ˙ New York

Alternative Synthetic Strategies for Enantioselective Construction of Halogenated Chiral Carbon Centers

Kazutaka Shibatomi*
Department of Materials Science, Toyohashi University of Technology, 1-1 Hibarigaoka, Tempaku-cho, Toyohashi 441-8580, Japan
Fax: +81(532)485833; e-Mail: shiba@tutms.tut.ac.jp;
Further Information

Publication History

Received 14 March 2010
Publication Date:
07 July 2010 (online)

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Abstract

This review focuses on the enantioselective synthesis of halogenated molecules having a chiral halocarbon center. In particular, this review discusses enantioselective transformations with haloalkenes and enantioselective α-substitutions of α-halo carbonyl compounds. Enantioselective halogen-transfer reactions are excluded from this review.

1 Introduction

2 Enantioselective Transformations with Halogenated Alkenes

2.1 Diels-Alder Reactions

2.2 Cyclopropanations

2.3 Hydrogenations and Epoxidations

2.4 Conjugate Additions to Halogenated Alkenes and Miscellaneous Reactions

3 Enantioselective α-Functionalizations of α-Halo Carbonyl Compounds or Their Enolates

3.1 Aldol-type Reactions

3.2 Alkylations with Phase-Transfer Catalysts and Allylations with Palladium Catalysts

3.3 Conjugate Additions of α-Halo Carbonyl Compounds

3.4 Heterofunctionalizations and Protonations

4 Conclusions

Key words

halogens - fluorine - asymmetric synthesis - asymmetric catalysis - alkyl halides

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7

Endo/exo nomenclature is related to the stereochemistry of the carbonyl substituent.