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Asymmetric Michael Additions to Nitroalkenes
Author(s) -
Berner Otto Mathias,
Tedeschi Livio,
Enders Dieter
Publication year - 2002
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 - 10.1002/1099-0690(200206)2002:12<1877::aid-ejoc1877>3.0.co;2-u
Subject(s) - enantiopure drug , chemistry , michael reaction , enantioselective synthesis , conjugate , nucleophile , addition reaction , combinatorial chemistry , heteroatom , catalysis , organocatalysis , organic chemistry , nucleophilic addition , substrate (aquarium) , ring (chemistry) , mathematics , geology , mathematical analysis , oceanography
The asymmetric conjugate addition of various carbon and heteroatom nucleophiles to nitroalkenes as a tool for the construction of highly functionalized synthetic building blocks is presented. Diastereoselective, substrate‐controlled 1,4‐additions are also included. Besides auxiliary controlled asymmetric Michael additions, external asymmetric versions employing enantiopure additives, addition‐elimination processes with enantiopure leaving groups, and catalytic asymmetric syntheses are described. The use of the highly reactive nitroalkenes as Michael acceptors opens the way to synthetically very useful C−C and C−X bond‐forming reactions and subsequent transformations as is demonstrated by various applications. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)