Scope and limitations of the double [4+ 3]-cycloadditions of 2-oxyallyl cations to 2, 2'-methylenedifuran and derivatives

…, ME Schwenter, Y Shatz, SR Dubbaka…

Index: Meilert, Kai Torsten; Schwenter, Marc-Etienne; Shatz, Yuli; Dubbaka, Srinivas Reddy; Vogel, Pierre Journal of Organic Chemistry, 2003 , vol. 68, # 7 p. 2964 - 2967

Full Text: HTML

Citation Number: 23

Abstract

The reactivity of various 2-oxyallyl cations toward 2, 2'-methylenedifuran (1b), 2, 2'- (hydroxymethyl) difuran (1c), 2, 2'-(trimethylsilylmethylene) difuran (1d), and di (2-furyl) methanone (1e) has been explored. Difuryl derivatives 1c, 1d, and 1e refused to undergo formal double [4+ 3]-cycloadditions. Conditions have been found to convert 1b into meso-1, 1'-methylenedi [(1 R, 1'S, 5 S, 5'R)-(3) and (±)-1, 1'-methylenedi [(1 RS, 1'SR, 5 SR, 5'RS)- ...