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Highly Diastereoselective Tandem N‐Alkylation‐Mannich Reaction of α‐Imino Esters

Highly Diastereoselective Tandem N‐Alkylation‐Mannich Reaction of α‐Imino Esters The diastereoselective tandem N‐alkylation‐Mannich reaction of α‐imino esters has been achieved by using three sequential reactions: N‐ethylation with diethylaluminum chloride and ethylaluminum chloride, oxidation with benzoyl peroxide (BPO), and addition of lithium enolates or ketene silyl acetals, in which “E”‐ and “Z”‐lithium enolates or E‐ and Z‐ketene silyl acetals give the syn and anti products, respectively. DME=1,2‐dimethoxyethane; PMP=p‐methoxyphenyl. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Asian Journal of Organic Chemistry Wiley

Highly Diastereoselective Tandem N‐Alkylation‐Mannich Reaction of α‐Imino Esters

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References (39)

Publisher
Wiley
Copyright
Copyright © 2013 Wiley Subscription Services, Inc., A Wiley Company
ISSN
2193-5807
eISSN
2193-5815
DOI
10.1002/ajoc.201300010
Publisher site
See Article on Publisher Site

Abstract

The diastereoselective tandem N‐alkylation‐Mannich reaction of α‐imino esters has been achieved by using three sequential reactions: N‐ethylation with diethylaluminum chloride and ethylaluminum chloride, oxidation with benzoyl peroxide (BPO), and addition of lithium enolates or ketene silyl acetals, in which “E”‐ and “Z”‐lithium enolates or E‐ and Z‐ketene silyl acetals give the syn and anti products, respectively. DME=1,2‐dimethoxyethane; PMP=p‐methoxyphenyl.

Journal

Asian Journal of Organic ChemistryWiley

Published: Mar 1, 2013

Keywords: ; ; ; ;

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