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
Full Text: HTML
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 ...
Related Articles:
New Criterion of Aromaticity and Implications for the (4 n+ 2) π Rule
[Lee, Patrick S.; Sakai, Shogo; Hoerstermann, Peter; Roth, Wolfgang R.; Kallel, E. Adam; Houk Journal of the American Chemical Society, 2003 , vol. 125, # 19 p. 5839 - 5848]
New Criterion of Aromaticity and Implications for the (4 n+ 2) π Rule
[Lee, Patrick S.; Sakai, Shogo; Hoerstermann, Peter; Roth, Wolfgang R.; Kallel, E. Adam; Houk Journal of the American Chemical Society, 2003 , vol. 125, # 19 p. 5839 - 5848]
[Leigh, William J.; Postigo, J. Alberto Journal of the Chemical Society, Chemical Communications, 1993 , # 24 p. 1836 - 1838]