Premium
Asymmetric Three‐Component Strecker Reactions Catalyzed by trans ‐4‐Hydroxy‐ L ‐proline‐Derived N , N′ ‐Dioxides
Author(s) -
Wen Yuehong,
Gao Bo,
Fu Yingzi,
Dong Shunxi,
Liu Xiaohua,
Feng Xiaoming
Publication year - 2008
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200800319
Subject(s) - strecker amino acid synthesis , methylamine , chemistry , catalysis , proline , enantiomeric excess , aldehyde , recrystallization (geology) , enantiomer , stereochemistry , organic chemistry , enantioselective synthesis , amino acid , paleontology , biochemistry , biology
Novel trans ‐4‐hydroxy‐ L ‐proline‐derived N,N′ ‐dioxides have been developed and used as efficient organocatalysts for the one‐pot three‐component Strecker reaction with an aldehyde, (1,1‐diphenyl)methylamine, and TMSCN. Both aromatic and aliphatic aldehydes were found to be suitable substrates. The corresponding α‐amino nitriles were obtained in high yields with up to 95 % ee ( ee =enantiomeric excess) under mild conditions. Optically pure products could be obtained after a single recrystallization. The catalyst can be easily prepared from trans ‐4‐hydroxy‐ L ‐proline and a diamine in three steps. Based on the experimental results and the observed absolute configurations of the products, a possible transition state has been proposed to explain the origin of the asymmetric induction.