Volume 18, Issue 35
Preparative Organic Chemistry
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ChemInform Abstract: Role of Steric, Electrostatic, and Hydrogen Bonding Effects as Face Selectivity Controlling Factors in Nitrone Cycloadditions.

M. BURDISSO

M. BURDISSO

Dip. Chim. Org., Univ., 27100 Pavia, Italy

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R. GANDOLFI

R. GANDOLFI

Dip. Chim. Org., Univ., 27100 Pavia, Italy

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P. PEVARELLO

P. PEVARELLO

Dip. Chim. Org., Univ., 27100 Pavia, Italy

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A. RASTELLI

A. RASTELLI

Dip. Chim. Org., Univ., 27100 Pavia, Italy

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First published: September 1, 1987

Abstract

1,3-Dipolar cycloaddition reaction of the bicyclooctenes (II) with the nitrone (I) yields the syn- or anti-isoxazolidines (III) and (IV).

ChemInform Abstract

1,3-Dipolar cycloaddition reaction of the bicyclooctenes (II) with the nitrone (I) yields the syn- or anti-isoxazolidines (III) and (IV). Steric and electronic effects on the stereoselectivity of this reaction are discussed in comparison with the cycloaddition reaction of the nitrones (V) and (VI) with the bicyclic alkenes (VII) - (IX).

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