Volume 29, Issue 1
Isocyclic Compounds
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ChemInform Abstract: TADDOL—TiCl2 Catalyzed Diels—Alder Reactions: Unexpected Influence of the Substituents in the 2-Position of the Dioxolane Ring on the Stereoselectivity.

B. ALTAVA

B. ALTAVA

Dep. Quim. Org., Inst. Cienc. Mater. Aragon, CSIC-Univ. Zaragoza, E-50009 Zaragoza, Spain

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M. I. BURGUETE

M. I. BURGUETE

Dep. Quim. Org., Inst. Cienc. Mater. Aragon, CSIC-Univ. Zaragoza, E-50009 Zaragoza, Spain

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J. M. FRAILE

J. M. FRAILE

Dep. Quim. Org., Inst. Cienc. Mater. Aragon, CSIC-Univ. Zaragoza, E-50009 Zaragoza, Spain

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J. I. GARCIA

J. I. GARCIA

Dep. Quim. Org., Inst. Cienc. Mater. Aragon, CSIC-Univ. Zaragoza, E-50009 Zaragoza, Spain

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S. V. LUIS

S. V. LUIS

Dep. Quim. Org., Inst. Cienc. Mater. Aragon, CSIC-Univ. Zaragoza, E-50009 Zaragoza, Spain

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J. A. MAYORAL

J. A. MAYORAL

Dep. Quim. Org., Inst. Cienc. Mater. Aragon, CSIC-Univ. Zaragoza, E-50009 Zaragoza, Spain

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A. J. ROYO

A. J. ROYO

Dep. Quim. Org., Inst. Cienc. Mater. Aragon, CSIC-Univ. Zaragoza, E-50009 Zaragoza, Spain

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M. J. VICENT

M. J. VICENT

Dep. Quim. Org., Inst. Cienc. Mater. Aragon, CSIC-Univ. Zaragoza, E-50009 Zaragoza, Spain

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First published: 24 June 2010

Abstract

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ChemInform Abstract

An unexpected influence of the substitution of the dioxolane ring on the direction of asymmetric induction in a Diels—Alder reaction catalyzed by TiCl2—TADDOLates is observed. MM2 calculations of the structures and relative energies of the possible dienophile—catalyst complexes are presented to offer a tentative explanation.

chemical structure image

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