JOURNAL ARTICLE

First Enantioselective Catalytic Wittig Reaction

Thomas WernerMarcel HoffmannSunetra Deshmukh

Year: 2014 Journal:   European Journal of Organic Chemistry Vol: 2014 (30)Pages: 6630-6633   Publisher: Wiley

Abstract

Abstract Herein we present the first catalytic enantioselective Wittig reaction. Chiral mono‐ and diphosphines were employed as catalysts for the desymmetrization of a prochiral ketone. The reaction was performed under microwave dielectric heating as well as under conventional heating. Selected catalysts led to moderate to good yields and enantioselectivities. In the presence of (+)‐1,2‐bis[(2 S ,5 S )‐2,5‐dimethylphospholano]benzene [( S , S )‐Me‐DuPhos], an enantiomeric excess of up to 90 % was obtained.

Keywords:
Enantioselective synthesis Desymmetrization Chemistry Wittig reaction Diphosphines Catalysis Ketone Organic chemistry Enantiomeric excess Benzene

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62
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0.94
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Citation History

Topics

Asymmetric Hydrogenation and Catalysis
Physical Sciences →  Chemistry →  Inorganic Chemistry
Organophosphorus compounds synthesis
Physical Sciences →  Chemistry →  Organic Chemistry
Phosphorus compounds and reactions
Physical Sciences →  Chemistry →  Organic Chemistry

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