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Enantioselective organocatalytic diels-alder reactions: a density functional theory and kinetic isotope effects study

The mechanism and enantioselectivity of the organocatalytic Diels-Alder reaction were computationally investigated by density functional theory at the B3LYP/6-31G(d) level of theory. The uncatalyzed Diels-Alder reaction was also studied to explore the effect of the organocatalyst on this reaction in...

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Main Authors: Omar, N.Y.M., Zain, Sharifuddin Md, Rahman, N.A.
Format: Article
Published: 2011
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QD Chemistry
Online Access:http://eprints.um.edu.my/6072/
http://www.scopus.com/inward/record.url?eid=2-s2.0-79955477030&partnerID=40&md5=3e347262a520ee0064174de695b02f4f
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spelling my.um.eprints.60722019-10-25T09:25:34Z http://eprints.um.edu.my/6072/ Enantioselective organocatalytic diels-alder reactions: a density functional theory and kinetic isotope effects study Omar, N.Y.M. Zain, Sharifuddin Md Rahman, N.A. QD Chemistry The mechanism and enantioselectivity of the organocatalytic Diels-Alder reaction were computationally investigated by density functional theory at the B3LYP/6-31G(d) level of theory. The uncatalyzed Diels-Alder reaction was also studied to explore the effect of the organocatalyst on this reaction in terms of energetics, selectivity, and mechanism. The catalyzed reaction showed improved endo/exo selectivity, and the free energy of activation was significantly lowered in the presence of the catalyst. Both uncatalyzed and catalyzed reactions exhibited concerted asynchronous reaction mechanism with the degree of asynchronicity being more evident in the presence of the catalyst. The Corey's experimentally derived predictive selection rules for the outcome of the organocatalytic Diels-Alder reaction were also theoretically analyzed, and an excellent agreement was found between experiment and theory. © 2011 Wiley Periodicals, Inc. 2011 Article PeerReviewed Omar, N.Y.M. and Zain, Sharifuddin Md and Rahman, N.A. (2011) Enantioselective organocatalytic diels-alder reactions: a density functional theory and kinetic isotope effects study. Journal of Computational Chemistry, 32 (9). pp. 1813-1823. ISSN 01928651 http://www.scopus.com/inward/record.url?eid=2-s2.0-79955477030&partnerID=40&md5=3e347262a520ee0064174de695b02f4f 10.1002/jcc.21763
institution Universiti Malaya
building UM Library
collection Institutional Repository
continent Asia
country Malaysia
content_provider Universiti Malaya
content_source UM Research Repository
url_provider http://eprints.um.edu.my/
topic QD Chemistry
spellingShingle QD Chemistry
Omar, N.Y.M.
Zain, Sharifuddin Md
Rahman, N.A.
Enantioselective organocatalytic diels-alder reactions: a density functional theory and kinetic isotope effects study
description The mechanism and enantioselectivity of the organocatalytic Diels-Alder reaction were computationally investigated by density functional theory at the B3LYP/6-31G(d) level of theory. The uncatalyzed Diels-Alder reaction was also studied to explore the effect of the organocatalyst on this reaction in terms of energetics, selectivity, and mechanism. The catalyzed reaction showed improved endo/exo selectivity, and the free energy of activation was significantly lowered in the presence of the catalyst. Both uncatalyzed and catalyzed reactions exhibited concerted asynchronous reaction mechanism with the degree of asynchronicity being more evident in the presence of the catalyst. The Corey's experimentally derived predictive selection rules for the outcome of the organocatalytic Diels-Alder reaction were also theoretically analyzed, and an excellent agreement was found between experiment and theory. © 2011 Wiley Periodicals, Inc.
format Article
author Omar, N.Y.M.
Zain, Sharifuddin Md
Rahman, N.A.
author_facet Omar, N.Y.M.
Zain, Sharifuddin Md
Rahman, N.A.
author_sort Omar, N.Y.M.
title Enantioselective organocatalytic diels-alder reactions: a density functional theory and kinetic isotope effects study
title_short Enantioselective organocatalytic diels-alder reactions: a density functional theory and kinetic isotope effects study
title_full Enantioselective organocatalytic diels-alder reactions: a density functional theory and kinetic isotope effects study
title_fullStr Enantioselective organocatalytic diels-alder reactions: a density functional theory and kinetic isotope effects study
title_full_unstemmed Enantioselective organocatalytic diels-alder reactions: a density functional theory and kinetic isotope effects study
title_sort enantioselective organocatalytic diels-alder reactions: a density functional theory and kinetic isotope effects study
publishDate 2011
url http://eprints.um.edu.my/6072/
http://www.scopus.com/inward/record.url?eid=2-s2.0-79955477030&partnerID=40&md5=3e347262a520ee0064174de695b02f4f
_version_ 1648736037669699584
score 13.211869

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