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First Enantioselective Catalytic Wittig Reaction
Author(s) -
Werner Thomas,
Hoffmann Marcel,
Deshmukh Sunetra
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402941
Subject(s) - enantioselective synthesis , desymmetrization , chemistry , wittig reaction , diphosphines , catalysis , ketone , organic chemistry , enantiomeric excess , benzene
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.