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Cinchona Alkaloid Catalyzed Regio‐ and Enantioselective Allylic Amination of Morita–Baylis–Hillman Carbonates with Isatins
Author(s) -
Zhao MeiXin,
Chen MingXiao,
Tang WenHao,
Wei DengKe,
Dai TongLei,
Shi Min
Publication year - 2012
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.201200376
Subject(s) - amination , chemistry , cinchona , enantioselective synthesis , allylic rearrangement , organic chemistry , methyl acrylate , catalysis , polymer , copolymer
An efficient enantioselective allylic amination of Morita–Baylis–Hillman (MBH) carbonates derived from methyl acrylate and aromatic aldehydes with isatins has been realized in the presence of commercially available cinchona alkaloids. The allylic amination products were obtained in moderate‐to‐good yields (46–74 %) with moderate‐to‐good enantioselectivities (up to 89 % ee ) under mild conditions. The synthetic utility of the amination products has been well demonstrated by the facile synthesis of methyl (3 R ,4 R )‐10‐oxo‐4‐phenyl‐2,3,4,10‐tetrahydropyrimido[1,2‐ a ]indole‐3‐carboxylate.