The Journal of Organic Chemistry

The anti-selective Michael addition of allylic organometals to ethylidenemalonates and related compounds

Y Yamamoto, S Nishii

Index: Yamamoto, Yoshinori; Nishii, Shinji Journal of Organic Chemistry, 1988 , vol. 53, # 15 p. 3597 - 3603

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Citation Number: 38

Abstract

The reaction of ethylidenemalonates 3a and a-cyanocrotonates 3b with crotylorganometals 2 such as B, Ti, Zr, and Sn reagents produced the anti adduct 4 predominantly. Similarly, the Michael addition of y-alkoxysubstituted allylmetals 6 to 3 gave the anti adduct 7 preferentially. The Michael addition of crotyltin 2e and (y-(methoxymethoxy) allyl) tin 6d to nitroolefins 20 again produced the anti isomers (21 and 23, respectively) predominantly. ...