p-Nitrophenyl Ethylthioester in Enantioselective Organocatalytic Michael Additions: Different Behaviour of [beta]-Aryl and [beta]-Alkyl Enals

Although several nucleophiles derived from arylacetic acids have been described in catalysis via iminium activation, none have presented good enantioselectivity and reactivity with both [beta]-alkyl and [beta]-aryl enals. This study on the Michael addition of p-nitrophenylacetic thioesters suggests...

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Bibliographic Details
Published in:European journal of organic chemistry 2013-11, Vol.2013 (31), p.7067
Main Authors: Duce, Sara, Jorge, María, Alonso, Inés, Ruano, José Luis García, Cid, M Belén
Format: Article
Language:English
Subjects:
Behavior
Beta
Online Access:Get full text
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Summary:Although several nucleophiles derived from arylacetic acids have been described in catalysis via iminium activation, none have presented good enantioselectivity and reactivity with both [beta]-alkyl and [beta]-aryl enals. This study on the Michael addition of p-nitrophenylacetic thioesters suggests that this behavior is due to the different reactivity and distinct tendency to reversibility exhibited by these types of enal. Independent optimization of the conditions for [beta]-alkyl and [beta]-aryl enals provide good yields and enantioselectivities with both substrates, affording Michael adducts that are versatile building blocks for the preparation of an interesting variety of arylacetic acid derivatives. [PUBLICATION ABSTRACT]
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201300934