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A Bioinspired Ugi/Michael/Aza‐Michael Cascade Reaction in Aqueous Media: Natural‐Product‐like Molecular Diversity
Author(s) -
Santra Soumava,
Andreana Peter R.
Publication year - 2011
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.201103567
Subject(s) - michael reaction , stereocenter , cascade , natural product , ugi reaction , chemistry , sequence (biology) , transformation (genetics) , stereochemistry , combinatorial chemistry , organic chemistry , enantioselective synthesis , chromatography , catalysis , isocyanide , biochemistry , gene
Whole in one! A one‐pot microwave‐assisted reaction sequence that consists of an Ugi/Michael/aza‐Michael transformation gives access to quaternary spirocenters leading to Amaryllidaceae and Erythrina alkaloid like compounds (see scheme). The process produces four stereogenic centers and six contiguous bonds, and provides products with good to excellent yields and appreciable diastereoselectivity.