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One‐Step Catalytic Enantioselective α‐Quaternary 5‐Hydroxyproline Synthesis: An Asymmetric Entry to Highly Functionalized α‐Quaternary Proline Derivatives
Author(s) -
Breistein Palle,
Johansson Jonas,
Ibrahem Ismail,
Lin Shuangzheng,
Deiana Luca,
Sun Junliang,
Cordova Armando
Publication year - 2012
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.201100911
Subject(s) - enantioselective synthesis , stereocenter , chemistry , quaternary , catalysis , proline , combinatorial chemistry , organocatalysis , organic chemistry , stereochemistry , amino acid , biochemistry , paleontology , biology
The highly enantioselective cascade reaction between N ‐protected α‐cyanoglycine esters and α,β‐unsaturated aldehydes is disclosed. The reaction represents a one‐step entry to polysubstituted 5‐hydroxyproline derivatives having a quaternary α‐stereocenter generally in high yields with up to >95:5 dr and 99:1 er . It is also a direct catalytic two‐step entry to functionalized α‐quaternary proline derivatives.