Li(sec-Bu)3BH-Mediated Cyclohexane Annulation of 2,7-Nonadienedioic Diesters

Eiichi Yoshii; Kozo Hori; Keiichi Nomura; Kentaro Yamaguchi

doi:10.1055/s-1995-5267

Synlett 1995; 1995(SI): 568-570
DOI: 10.1055/s-1995-5267

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Li(sec-Bu)₃BH-Mediated Cyclohexane Annulation of 2,7-Nonadienedioic Diesters

Eiichi Yoshii^* , Kozo Hori, Keiichi Nomura, Kentaro Yamaguchi

^*Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University, Sugitani 2630, Toyama 930-01, Japan

Abstract

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Treatment of 1-t-butyl/9-methyl 2,7-nonadienedioates with L-Selectride afforded methyl 2-[t-butoxycarbonyl)ethyl]cyclohexane-1-carboxylates in fair to high yields arising from regioselective conjugate addition of the borohydride at the methyl enoate group and sequential intramolecular Michael addition. 1,2-Trans stereoselectivity was observed with the 2-methyl-, 2,4- and 4,4-dimethyl-, and 4,4,8-trimethylnonadienedioates, while unsubstituted and 4-methyl compounds favored production of 1,2-cis isomers.

tandem Michael reaction - cyclohexane annulation - L-Selectride - 2,7-nonadienedioate - stereoselectivity

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