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Synlett 1991; 1991(9): 603-610
DOI: 10.1055/s-1991-20813
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Chiral Nitroolefins for Enantioselective Reactions

K. Fuji* , M. Node
  • *Institute for Chemical Research, Kyoto University, Uji, Kyoto 611, Japan
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Publication Date:
07 March 2002 (online)

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Nitroolefins are important intermediates in organic synthesis because of their versatile functional group transformations.Their synthetic potential should be greatly enhanced, if they contain a quaternary carbon in optically active form. We have developed a new method for the construction of nitroolefins which meet such requirements. In the reaction of enolates with nitroolefins having a chiral hetero group at the ß-position, the hetero substituent is replaced by a carbon substituent through an addition-elimination process. The scope, limitations, and the mechanism for the asymmetric induction are discussed. 1. Introduction 2. Synthesis and Reactivity of ß-Heterosubstituted Nitroolefins 2.1. Nitro Enamines 2.2. ß-Nitrovinyl Sulfides and Sulfoxides 3. Asymmetric Syntheses with Chiral Nitroolefins 3.1. Construction of Chiral Quaternary Carbon Centers Through an Addition-Elimination Process with Chiral Nitro Enamines 3.2. Enantioselective Reactions with Chiral ß-Nitrovinyl Sulfoxides 4. Conclusions