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Enantioselective Activation of Aldehydes by Chiral Phosphoric Acid Catalysts in an Aza‐ene‐type Reaction between Glyoxylate and Enecarbamate
Author(s) -
Terada Masahiro,
Soga Kazuyo,
Momiyama Norie
Publication year - 2008
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200800232
Subject(s) - phosphoric acid , glyoxylate cycle , enantioselective synthesis , catalysis , ene reaction , aldehyde , chemistry , type (biology) , organic chemistry , combinatorial chemistry , enzyme , biology , ecology
Double interaction does it : Highly enantio‐ and diastereoselective aza‐ene‐type reaction of glyoxylate with an enecarbamate is accomplished by using a binol‐derived phosphoric acid catalyst (see scheme). DFT computational analysis revealed that two hydrogen bonds formed between the catalyst and the aldehyde are critical for the high enantioselectivity.