Journal
TETRAHEDRON
Volume 56, Issue 25, Pages 4213-4218Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4020(00)00346-X
Keywords
Diels-Alder reactions; ketene acetals; regiochemistry; zwitterions
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The regioselectivity of the two-step Diels-Alder reaction of unsymmetrically substituted tetrazines 4 with 2-cyclopropylidene-imidazolidine 6 is investigated. The first reversible step of the cycloaddition affording zwitterions 7 and 8 is controlled by steric effects, which are explained using a simple model. The overall regioselectivity, however, is determined in the second step of the cycloaddition or at an even later stage. (C) 2000 Elsevier Science Ltd. All rights reserved.
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