Parity Reversal: A New Diels-Alder Strategy for the Synthesis of Sesquinorbornadienes, Including Those with Heterobridges and Those of Unusual Stereochemistry

Douglas N. Butler; Davor Margetic; Peter J. C. O'Neill; Ronald N. Warrener

doi:10.1055/s-2000-6445

Synlett 2000; 2000(1): 98-100
DOI: 10.1055/s-2000-6445

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Parity Reversal: A New Diels-Alder Strategy for the Synthesis of Sesquinorbornadienes, Including Those with Heterobridges and Those of Unusual Stereochemistry

Douglas N. Butler^* , Davor Margetic, Peter J. C. O'Neill, Ronald N. Warrener

^*Centre for Molecular Architecture, Central Queensland University, Rockhampton, Queensland, 4702, Australia; Fax + 61 749 30 99 17; E-mail: r.warrener@cqu.edu.au

Abstract

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The concept of parity reversal, where interchange of the substituent at the 5-position of a cyclic 5-membered 1,3-diene with the substituent at the 7-position of a norbornadiene anhydride, provides two sets of Diels-Alder reagents which each yield mixtures of exo-face adducts, one member of which always corresponds to the rare endo-face adduct of the parity reversal combination. AM1, ab initio and higher order calculations of TS energies are used to predict outcomes.

Diels-Alder cycloaddition - norbornadiene anhydrides - endo-adducts - hetero-bridged sesquinorbornadienes - AM1 - ab initio

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