Cycloaddition chemistry of 1, 3-and 2, 3-bis (phenylsulfonyl)-1, 3-dienes with enamines and ynamines

…, Y Gareau, B Harrison, A Rodriguez

Index: Padwa, Albert; Gareau, Yves; Harrison, Brian; Rodriguez, Augusto Journal of Organic Chemistry, 1992 , vol. 57, # 13 p. 3540 - 3545

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Abstract

1, 3-and 2, 3-bis (phenylsulfonyl) dienes were found to react smoothly with a variety of enamines and enamine equivalents to give [4+ 2]-cycloadduds in excellent yields. The cycloaddition proceeds with high regioselectivity affording carbucycles as well as heterocycles. The reactivity of the 1, 3-i" er was found to be much greater than the 2, 3- isomer and is a consequence of both conformational and electronic factors. Formation of ...