N-PROLINYLANTHRANILAMIDE BASED ORGANOCATALYSTS FOR ASYMMETRIC ALDOL REACTIONS

Bibliographic Details
Main Author:	panda, santanu
Language:	English
Published:	Case Western Reserve University School of Graduate Studies / OhioLINK 2013
Subjects:	Chemistry
Online Access:	http://rave.ohiolink.edu/etdc/view?acc_num=case1371815461

id	ndltd-OhioLink-oai-etd.ohiolink.edu-case1371815461
record_format	oai_dc
spelling	ndltd-OhioLink-oai-etd.ohiolink.edu-case13718154612021-08-03T05:24:22Z N-PROLINYLANTHRANILAMIDE BASED ORGANOCATALYSTS FOR ASYMMETRIC ALDOL REACTIONS panda, santanu Chemistry The use of organocatalysts promises to allow organic reactions to proceed with high selectivity (regio and stereo) without the intervention of organometallic catalysts, some of which pose problems for use on large scale, and their eventual disposal. The aldol reaction is one of the most important C-C bond-forming reactions in organic synthesis. L-proline has been reported as a catalyst for inter and intramolecular aldol reactions but it suffers with compatibility with many solvents, racemic products from reactions in water and oxazolidinone formation which impairs catalytic efficiency. Several N-prolinylanthranilic acid derivatives were prepared and tested as bifunctional organocatalysts in the direct asymmetric aldol reaction of cyclohexanone with p-nitrobenzaldehyde. It was found that methyl substitution ortho to the carboxylic acid improves enantioselectivity, but substitution ortho to the anilide group does not. The catalyst 2.19 derived from 2-amino-6-methylbenzoic acid was tested over a range of direct asymmetric aldol reactions and its overall performance is equal to or better than many of the known prolinamide catalysts in terms of yield, diastereoselectivity, and enantioselectivity 2013-08-23 English text Case Western Reserve University School of Graduate Studies / OhioLINK http://rave.ohiolink.edu/etdc/view?acc_num=case1371815461 http://rave.ohiolink.edu/etdc/view?acc_num=case1371815461 unrestricted This thesis or dissertation is protected by copyright: some rights reserved. It is licensed for use under a Creative Commons license. Specific terms and permissions are available from this document's record in the OhioLINK ETD Center.
collection	NDLTD
language	English
sources	NDLTD
topic	Chemistry
spellingShingle	Chemistry panda, santanu N-PROLINYLANTHRANILAMIDE BASED ORGANOCATALYSTS FOR ASYMMETRIC ALDOL REACTIONS
author	panda, santanu
author_facet	panda, santanu
author_sort	panda, santanu
title	N-PROLINYLANTHRANILAMIDE BASED ORGANOCATALYSTS FOR ASYMMETRIC ALDOL REACTIONS
title_short	N-PROLINYLANTHRANILAMIDE BASED ORGANOCATALYSTS FOR ASYMMETRIC ALDOL REACTIONS
title_full	N-PROLINYLANTHRANILAMIDE BASED ORGANOCATALYSTS FOR ASYMMETRIC ALDOL REACTIONS
title_fullStr	N-PROLINYLANTHRANILAMIDE BASED ORGANOCATALYSTS FOR ASYMMETRIC ALDOL REACTIONS
title_full_unstemmed	N-PROLINYLANTHRANILAMIDE BASED ORGANOCATALYSTS FOR ASYMMETRIC ALDOL REACTIONS
title_sort	n-prolinylanthranilamide based organocatalysts for asymmetric aldol reactions
publisher	Case Western Reserve University School of Graduate Studies / OhioLINK
publishDate	2013
url	http://rave.ohiolink.edu/etdc/view?acc_num=case1371815461
work_keys_str_mv	AT pandasantanu nprolinylanthranilamidebasedorganocatalystsforasymmetricaldolreactions
_version_	1719419711485116416

N-PROLINYLANTHRANILAMIDE BASED ORGANOCATALYSTS FOR ASYMMETRIC ALDOL REACTIONS

Similar Items