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Model Studies on the Enzyme‐Regulated Stereodivergent Cascade Passerini Reaction
Author(s) -
Wilk Monika,
Brodzka Anna,
Koszelewski Dominik,
SamsonowiczGórski Jan,
Ostaszewski Ryszard
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202100760
Subject(s) - chemistry , stereocenter , kinetic resolution , cascade , enzyme , stereochemistry , combinatorial chemistry , cascade reaction , biocatalysis , organic chemistry , enantioselective synthesis , catalysis , reaction mechanism , chromatography
The synthesis of chiral α‐acyloxy carboxamides containing two stereogenic centers continues to be a challenging field of organic chemistry. Herein, we have proposed and proved the feasibility of an enzyme regulated‐cascade reaction, which using the same substrates enables the formation of individual stereoisomers of α ‐acyloxy carboxamides with up to 99 % ee . The access to the individual stereoisomeric products has been achieved by a combination of the enzymatic kinetic resolution of racemic vinyl esters, subsequent Passerini reaction, and enzymatic kinetic resolution of formed α ‐acyloxy carboxamides. The presented studies are promising in exploratory proof‐of‐concept of enzyme‐controlled stereodivergent cascade to form an important class of chiral compounds for medicinal chemistry.