The Proline‐Catalyzed Double Mannich Reaction of Acetaldehyde with  N ‐Boc Imines | Zendy

Chandler Carley | Zendy; Galzerano Patrizia | Zendy; Michrowska Anna | Zendy; List Benjamin | Zendy

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The Proline‐Catalyzed Double Mannich Reaction of Acetaldehyde with N ‐Boc Imines

Author(s) -

Chandler Carley,

Galzerano Patrizia,

Michrowska Anna,

List Benjamin

Publication year - 2009

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.200806049

Subject(s) - acetaldehyde , mannich reaction , chemistry , diastereomer , catalysis , proline , double bond , organic chemistry , medicinal chemistry , stereochemistry , amino acid , biochemistry , ethanol

Double‐cross : Proline catalyzes the double Mannich reaction of acetaldehyde with N ‐Boc imines in excellent yields (up to 99 %; Boc= tert ‐butoxycarbonyl) and close to perfect diastereo‐ and enantioselectivities. Depending on the choice of catalysts, both the chiral, pseudo‐ C 2 ‐symmetric diastereomer and the corresponding meso compound can be prepared. Cross double Mannich reactions of acetaldehyde with two different imines are also demonstrated.

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