Examination of homo-[3 + 2]-dipolar cycloaddition: mechanistic insight into regio- and diastereoselectivity.

Examination of homo-[3 + 2]-dipolar cycloaddition: mechanistic insight into regio- and diastereoselectivity. Research Abstract Details 

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Examination of homo-[3 + 2]-dipolar cycloaddition: mechanistic insight into regio- and diastereoselectivity. Abstract Text:

Avedis Karadeolian,Michael A Kerr,Avedis Karadeolian,Michael A Kerr,Avedis Karadeolian,Michael A Kerr,

The reaction of 2,3-disubstituted-1,1-cyclopropanediesters with nitrones under Lewis acid conditions produces tetrahydro-1,2-oxazines in which the cis/trans relationship of the cyclopropanes is not conserved. Reacting nitrones with 2,3-cis-disubstituted cyclopropanes lead to 5,6-trans-oxazines, and 2,3-trans-disubstituted cyclopropanes lead to 5,6-cis-oxazines. This observed stereochemical inversion provides evidence for a stepwise annulation mechanism in the preparation of tetrahydro-1,2-oxazines.

Examination of homo-[3 + 2]-dipolar cycloaddition: mechanistic insight into regio- and diastereoselectivity. Publishing Authors By Initials

A Karadeolian,MA Kerr,A Karadeolian,MA Kerr,A Karadeolian,MA Kerr,

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Examination of homo-[3 + 2]-dipolar cycloaddition: mechanistic insight into regio- and diastereoselectivity. Journal Published:

PUBLICATION TYPE: Journal Article

Journal: The Journal of organic chemistry

VOLUME: 72

Page Numbers: 10251-3

Journal Abbreviation: J. Org. Chem.

ISSN: 0022-3263

DAY: 14

MONTH: 11

YEAR: 2007

Examination of homo-[3 + 2]-dipolar cycloaddition: mechanistic insight into regio- and diastereoselectivity. Information

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LANGUAGE: eng

NlmUniqueID: 2985193

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Grant and Affiliation Information for Examination of homo-[3 + 2]-dipolar cycloaddition: mechanistic insight into regio- and diastereoselectivity.

AFFILIATION: Department of Chemistry, The University of Western Ontario, London, Ontario, Canada, N6A 5B7 makerr@uwo.ca.

Country: United States

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MEDLINETA: J Org Chem

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