Amino alcohol-mediated enantioselective syntheses of 伪-substituted indanones and tetralones, ammonium enolates as key intermediates

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• 作者：Jacques Muzart ; ^{jacques.muzart@univ-reims.fr" class="auth_mail}
• 刊名：Tetrahedron: Asymmetry
• 出版年：15 May 2014
• 年：2014
• 卷：25
• 期：9
• 页码：697-704
• 全文大小：1678 K

文摘

Optically active 2-substituted-1-indanones or 2-substituted-1-tetralones are isolated from amino alcohol-mediated asymmetric domino reactions of 伪-disubstituted ketones, 尾-ketoesters, enol carbonates, 伪,尾-unsaturated ketones, a silyl enol ether, or a 尾-ketoacid, with some of these reactions occurring under UV-light irradiation or Pd catalysis. The absence of a relationship between the nature of the substrate and the absolute configuration of the ketone produced is due to the protonation of a common ammonium enolate as the key enantioselective step. The enantioselectivity depends on various factors, which indicates the occurrence of side pathways.