2, 3-Bis (phenylsulfonyl)-1, 3-butadiene: Substrate for Michael Donor/Acceptors in a Novel Synthesis of Fused Cyclopentenes

…, SS Murphree, Z Ni, SH Watterson

Index: Padwa, Albert; Murphree, S. Shaun; Ni, Zhijie; Watterson, Scott H. Journal of Organic Chemistry, 1996 , vol. 61, # 11 p. 3829 - 3838

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Citation Number: 28

Abstract

The reaction of 2, 3-bis (phenylsulfonyl)-1, 3-butadiene with the anion of various 1- substituted dimethyl 1-pentenedioates has been investigated with the purpose of devising a tandem conjugate addition-[3+ 2]-anionic cyclization route for the synthesis of bicyclo [3.3. 0] octenes. The reaction proceeds with complete stereospecificity as was evidenced by treating (E)-and (Z)-dimethyl (3-cyano-2-propenyl) propanedioate with NaH in the presence of the ...