One‐Step Catalytic Enantioselective α‐Quaternary 5‐Hydroxyproline Synthesis: An Asymmetric Entry to Highly Functionalized α‐Quaternary Proline Derivatives | Zendy

Breistein Palle | Zendy; Johansson Jonas | Zendy; Ibrahem Ismail | Zendy; Lin Shuangzheng | Zendy; Deiana Luca | Zendy; Sun Junliang | Zendy; Cordova Armando | Zendy

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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.

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