NDLI: Umpolung Reactions of -Imino Esters: Useful Methods for the Preparation of -Amino Acid Frameworks.

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Umpolung Reactions of -Imino Esters: Useful Methods for the Preparation of -Amino Acid Frameworks.

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Mizota, Isao Shimizu, Makoto
Description	Country affiliation: Japan Author Affiliation: Mizota I ( Department of Chemistry for Materials, Graduate School of Engineering Mie University, Tsu Mie, 514-8507, Japan.); Shimizu M ( Department of Chemistry for Materials, Graduate School of Engineering Mie University, Tsu Mie, 514-8507, Japan.)
Abstract	This paper summarizes our recent efforts toward the development of tandem reactions utilizing umpolung reactions of -imino esters. A highly diastereoselective tandem N-alkylation-Mannich reaction of -imino esters was developed. A tandem N-alkylation-addition reaction of -imino esters derived from ethyl glyoxylate with various aldehydes proceeded to give 1,2-amino alcohols. The same reaction also proceeded efficiently using a novel flow system comprising two connected microreactors. Novel syntheses of -quaternary alkynyl amino esters and allenoates were developed through the use of umpolung N-addition to ß,Î³-alkynyl -imino esters, followed by regioselective acylation. In addition, a highly regioselective tandem N-alkylation-vinylogous aldol reaction of ß,Î³-alkenyl -imino esters was discovered. N-Alkylation of -iminophosphonates followed by a Horner-Wadsworth-Emmons reaction with aldehydes occurred to afford enamines, which can be used in a four-component coupling reaction with methyl vinyl ketone. -N-Acyloxyimino esters served as highly efficient substrates for the N,N,C-trialkylation reaction to introduce various nucleophiles at the imino nitrogen and carbon atoms.
File Format	HTM / HTML
ISSN	15278999
Issue Number	2
Journal	The Chemical Record
Volume Number	16
e-ISSN	15280691
Language	English
Publisher	Wiley
Publisher Date	2016-04-01
Publisher Place	United States
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Discipline Chemistry
Content Type	Text
Resource Type	Article
Subject	Biochemistry (medical) Chemistry Materials Chemistry Biochemistry Chemical Engineering

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