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A Highly Reactive and Enantioselective Bifunctional Organocatalyst for the Methanolytic Desymmetrization of Cyclic Anhydrides: Prevention of Catalyst Aggregation
Author(s) -
Oh Sang Ho,
Rho Ho Sik,
Lee Ji Woong,
Lee Je Eun,
Youk Sung Hoon,
Chin Jik,
Song Choong Eui
Publication year - 2008
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200801636
Subject(s) - enantioselective synthesis , desymmetrization , chemistry , cinchona , stereoselectivity , bifunctional , catalysis , reactivity (psychology) , organocatalysis , organic chemistry , stereochemistry , combinatorial chemistry , medicine , alternative medicine , pathology
Unprecedented reactivity and high stereoselectivity were observed in the ring opening of meso anhydrides under mild conditions with a cinchona‐alkaloid‐based sulfonamide catalyst (see scheme). Computation of the catalyst–transition‐state analogue (right; gray C, white H, green F, blue N, red O, yellow S) provided insight into the origin of the stereoselectivity.