Electronic control of stereoselectivity. 19. Stereoselection in [4+ 2] cycloadditions to anti, anti-2, 3-diethylidenenorbornane and-norbornene. Crystal structure analysis …

LA Paquette, AG Schaefer…

Index: Paquette,L.A.; Schaefer,A.C.; Blount,J.F. Journal of the American Chemical Society, 1983 , vol. 105, p. 3642

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Citation Number: 32

Abstract

Abstract: Diels-Alder addition of anti, anti-2, 3-diethylidenenorbornane (4) to N- phenylmaleimide, p-benzoquinone, phenyl vinyl sulfone, and dimethyl acetylenedicarboxylate (DMAD) gave exclusively products resulting from below-plane dienophile capture. In contrast, N-methyltriazolinedione (MTAD) added to 4 with overwhelmingly preferred above-plane stereoselection. Where the less reactive ...

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