Stereoselectivity in the Cycloaddition of Cyclopentadiene to N-Fumaroyl-[2R, S (R)]-Bornane-10, 2-sulfinamide Monomethyl Ester

…, R Kawecki, Z Urbanczyk-Lipkowska

Index: Chapuis, Christian; Kawecki, Robert; Urbanczyk-Lipkowska, Zofia Helvetica Chimica Acta, 2001 , vol. 84, # 3 p. 579 - 588

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Citation Number: 9

Abstract

The cyclic [2R, S (R)]-bornane-10, 2-sulfinamide (À)-2b, an analogue of Oppolzer s camphor- derived sultam (À)-2a, was synthesized by reduction of the known N-alkylidenesulfinamide ()-1b with NaBH4. The uncatalyzed [4 2] cycloaddition of cyclopentadiene to the methyl ester (À)-3b of the N-fumaroylsulfinamide, obtained from (À)-2b, proceeds with lower endo and p- facial selectivity as compared to dienophiles (À)-3a, c. In contrast to these latter, the ...