Direct Enantioselective Conjugate Addition of Carboxylic Acids with Chiral Lithium Amides as Traceless Auxiliaries | Zendy

Ping Lu | Zendy; Jeffrey J. Jackson | Zendy; John A. Eickhoff | Zendy; Armen Zakarian | Zendy

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Direct Enantioselective Conjugate Addition of Carboxylic Acids with Chiral Lithium Amides as Traceless Auxiliaries

Author(s) -

Ping Lu,

Jeffrey J. Jackson,

John A. Eickhoff,

Armen Zakarian

Publication year - 2015

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/ja512213c

Subject(s) - enantioselective synthesis , chemistry , reagent , lithium (medication) , conjugate , organic chemistry , michael reaction , carboxylic acid , heteroatom , carbon fibers , dilithium , combinatorial chemistry , addition reaction , catalysis , ring (chemistry) , mathematical analysis , materials science , mathematics , composite number , composite material , endocrinology , ion , deprotonation , medicine

Michael addition is a premier synthetic method for carbon-carbon and carbon-heteroatom bond formation. Using chiral dilithium amides as traceless auxiliaries, we report the direct enantioselective Michael addition of carboxylic acids. A free carboxyl group in the product provides versatility for further functionalization, and the chiral reagent can be readily recovered by extraction with aqueous acid. The method has been applied in the enantioselective total synthesis of the purported structure of pulveraven B.

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