Cinchona‐Alkaloid‐Catalyzed Enantioselective Direct Aldol‐Type Reaction of Oxindoles with Ethyl Trifluoropyruvate | Zendy

Ogawa Shinichi | Zendy; Shibata Norio | Zendy; Inagaki Junji | Zendy; Nakamura Shuichi | Zendy; Toru Takeshi | Zendy; Shiro Motoo | Zendy

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Cinchona‐Alkaloid‐Catalyzed Enantioselective Direct Aldol‐Type Reaction of Oxindoles with Ethyl Trifluoropyruvate

Author(s) -

Ogawa Shinichi,

Shibata Norio,

Inagaki Junji,

Nakamura Shuichi,

Toru Takeshi,

Shiro Motoo

Publication year - 2007

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.200703317

Subject(s) - stereocenter , enantioselective synthesis , trifluoromethyl , chemistry , cinchona , enantiomer , aldol reaction , organic chemistry , organocatalysis , alcohol , cinchona alkaloids , moiety , stereochemistry , combinatorial chemistry , alkyl , catalysis

One or t'other : Pseudoenantiomeric cinchona alkaloids can be used as organocatalysts to access both enantiomeric products of the title reaction selectively in high yields with high diastereo‐ and enantioselectivities (up to 99 % ee ; see scheme). One of the two contiguous quaternary stereogenic carbon centers that are constructed simultaneously is a pharmaceutically significant tertiary α‐trifluoromethyl alcohol center. R 1 =alkyl; R 2 =H, Me.

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