Investigation of the cycloaddition of C,N-diarylnitrones to methyl cinnamate under different reaction conditions were carried out. Two diastereoisomeric and one regioisomeric cycloadducts were isolated and characterized by spectroscopic and X-ray data. Remarkable change in selectivity was noticed in solvent-free condition and in the presence of ytterbium triflate as catalyst. © 2011 Taylor & Francis Group, LLC.

P K BISWAS

D BANDYOPADHYAY

A BANERJI

University of Calcutta (informally known as Calcutta University or CU) is a collegiate public state university located in Kolkata, West Bengal, India.&nbsp;Within India it is recognized as a &quot;Five-Star University&quot; and accredited &quot;A&quot; Grade by National Assessment and Accreditation Council.

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The University of Calcutta has secured the Fifth position among the Universities of India in the prestigious &quot;Indian University Ranking 2019&quot; list, released by the NIRF of the Ministry of Human Resource Development, Government of India.

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It was established on 24 January 1857, and was one of the first institutions in Asia to be established as a multidisciplinary and Western-style university. Its alumni and faculty include several heads of state, heads of government, social reformers, prominent artists, only academy award winner and Dirac medal winner in India, many Fellows of the Royal Society and five Nobel laureates as of 2019 which is highest in South Asia.

University Of Calcutta

Remarkable stereocontrol in 1,3-dipolar cycloaddition of acyclic nitrones: Investigation of the cycloaddition of C,N-diaryl nitrones to methyl cinnamate under different reaction conditions

Synthetic Communications

(Chemical Equation Presented) Investigation of cycloadditions of C-aryl-N-(4-chlorophenyl)nitrones to N-cinnamoyl piperidines was carried out. Two diastereoisomeric and one regioisomeric cycloadducts, and in some cases ring-opened compounds were characterized by spectroscopic and X-ray data. Molecular modelling was carried out for conformational studies.

Journal of Heterocyclic Chemistry

1,3-Dipolar cycloadditions: Investigation of cycloadditions of C-aryl-N-(4-chlorophenyl) nitrones to N-cinnamoyl piperidines

A series of cycloadducts possessing unusual flipping modes have been isolated from the 1,3-dipolar cycloaddition of 3,4,5,6-tetrahydropyridine N-oxide to piperidides of cinnamic acid and para-substituted cinnamic acids and these were analyzed by X-ray crystallography to reveal novel solid-state structures. The presence of two different flippomers arising due to flipping of the six/five bicyclic ring was confirmed both in solid state and in solution. This is the first observation of 1,3-dipolar cycloadducts having two different flippomers arising due to flipping of the isoxazolidine ring. © 2006 Elsevier Ltd. All rights reserved.

Tetrahedron Letters

The first report of unusual flipping of the cycloadducts from 1,3-dipolar cycloaddition of 3,4,5,6-tetrahydropyridine N-oxide to N-cinnamoyl piperidines

A series of unexpected cycloadducts along with normal cycloadducts have been isolated from the 1,3-dipolar cycloaddition of 3,4-dehydromorpholine N-oxide to piperidides of cinnamic acid and para-substituted cinnamic acids and these were analyzed by X-ray crystallography to reveal novel solid-state structures. At first, 1:1 cycloadducts were formed which underwent in situ nucleophilic attack by another reduced nitrone moiety. A plausible iminium-oxonium ion mechanism has been proposed. © 2005 Elsevier Ltd. All rights reserved.

Unexpected cycloadducts from 1,3-dipolar cycloaddition of 3,4-dehydromorpholine N-oxide to N-cinnamoyl piperidines-first report of the novel formation of 2:1 cycloadducts

Studies on cycloadditions of C,N-diarylnitrones to cinnamic acid amides were carried out. The diastereoisomeric (I, II) and (in some cases) regioisomeric (III) cycloadducts obtained were characterized by spectroscopic and X-ray data. Conformational studies were carried out by molecular modelling.

Monatshefte für Chemie - Chemical Monthly

1,3-Dipolar cycloadditions VI [1]. Structure and conformation of cycloadducts from reactions of C-aryl-N-phenylnitrones with substituted cinnamic acid amides

Journal	Synthetic Communications
Publisher	TAYLOR & FRANCIS INC
ISSN	0039-7911