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Catalytic Enantioselective Aza‐Henry Reactions
Author(s) -
MarquésLópez Eugenia,
Merino Pedro,
Tejero Tomás,
Herrera Raquel P.
Publication year - 2009
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.200801097
Subject(s) - enantioselective synthesis , chemistry , catalysis , organocatalysis , combinatorial chemistry , organic chemistry , organic synthesis , vicinal , mannich reaction , organic reaction
Asymmetric aza‐Henry reactions provide excellent routes for the synthesis of optically active organic compounds bearing two vicinal different nitrogenated functionalities that can be further transformed into a variety of interesting compounds such as 1,2‐diamines or α‐amino acids. The catalytic asymmetric version of the reaction (also called the nitro‐Mannich reaction) provides highly efficient access to enantiomerically pure compounds. Both metal‐based and organic catalysts can be used to promote these reactions in a enantioselective way; in particular, a great variety of different organocatalysts – including thioureas, N ‐oxides, quaternary ammonium salts and chiral Brønsted acids – have demonstrated their efficiency, as has recently been reported by several research groups. In addition, considerable effort is being made in controlling the syn / anti diastereoselectivities of these reactions when substituted nitroalkanes are used as substrates. In this microreview recent advances, including scope and limitations, are discussed and applications of different catalytic systems for catalytic asymmetric aza‐Henry reactions are presented.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)