Revisiting [3+ 3] route to 1, 3-cyclohexanedione frameworks: hidden aspect of thermodynamically controlled enolates

…, R Kadoya, M Arai, H Takahashi, Y Kaisi…

Index: Ishikawa, Teruhiko; Kadoya, Ryuichiro; Arai, Masaki; Takahashi, Haruka; Kaisi, Yumi; Mizuta, Tomohiro; Yoshikai, Kazusa; Saito, Seiki Journal of Organic Chemistry, 2001 , vol. 66, # 24 p. 8000 - 8009

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Citation Number: 29

Abstract

We have revisited the traditional consecutive Michael-Claisen [3+ 3] process (MC-[3+ 3]) promising the synthesis of a cyclohexane-1, 3-dione derivatives from nonactivated simple ketones and enoates and evaluated its potential in modern organic synthesis. Twenty to thirty examples were demonstrated to be effective. The reactions exhibited remarkable regioselectivity with the Michael addition proceeding through nucleophilic attack by the ...