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Lewis Acid‐Catalyzed [3+2] Cycloaddition of Donor‐Acceptor Cyclopropanes and Enamines: Enantioselective Synthesis of Nitrogen‐Functionalized Cyclopentane Derivatives
Author(s) -
Verma Kamal,
Banerjee Prabal
Publication year - 2016
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201600221
Subject(s) - chemistry , cyclopentane , enantioselective synthesis , hydrogenolysis , cycloaddition , catalysis , lewis acids and bases , enantiomer , organic chemistry , enantiomeric excess
A straightforward and efficient method for the synthesis of nitrogen‐functionalized cyclopentane derivatives via [3+2] cycloaddition of enamines with donor‐acceptor cyclopropanes in the presence of catalytic amounts of various Lewis acids at room temperature has been developed; furthermore, the corresponding β‐amino acid was synthesized by monodecarboxylation and hydrogenolysis. An enantioenriched synthesis of nitrogen‐functionalized cyclopentane derivatives through dynamic kinetic asymmetric transformation of racemic donor‐acceptor cyclopropanes has also been achieved employing a copper complex [Cu(OTf) 2 ‐ L1 ] as the catalyst affording an enantiomeric ratio up to 8:1.