Bifunctional organocatalysts containing primary amines for asymmetric Michael additions

  • The asymmetric Michael addition of nucleophilic carbonyls (via enamine) to a diverse number of Michael acceptors produces an important carbon-carbon bond, producing a truly large number of products. Over the past decade an enormous number of organocatalysts have been developed for the asymmetric Michael addition. Challenging nucleophilic carbonyl additions, e.g. a-substituted carbonyls and some cyclic carbonyls, e.g. cyclopentanone, remain and require attention in terms of stereoselectivity, catalyst loading reaction time and yield. Here we have focused on designing new organocatalysts with primary amines to overcome the above outlined challenges. We have developed two types of organocatalysts: 1) primarytertiary diamine organocatalysts and 2) non-covalent bifunctional organocatalysts. Diamines were found to be better organocatalysts for the asymmetric Michael addition of cyclopentanone to various nitroolefins. While the assembled catalysts were found to be superior for the asymmetric Michael addition of a-substituted aldehydes addition to maleimides.

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Publishing Institution:IRC-Library, Information Resource Center der Jacobs University Bremen
Granting Institution:Jacobs Univ.
Author:Abdul Sadiq
Referee:Thomas Nugent, Nikolai Kuhnert, Muhammad Sharif Akbar
Advisor:Thomas Nugent
Persistent Identifier (URN):urn:nbn:de:101:1-2013052811939
Document Type:PhD Thesis
Language:English
Date of Successful Oral Defense:2011/12/15
Date of First Publication:2012/01/19
PhD Degree:Chemistry
School:SES School of Engineering and Science
Library of Congress Classification:Q Science / QD Chemistry / QD241-441 Organic chemistry
Call No:Thesis 2011/46

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