Preparation of chiral building blocks for the enantioselective total synthesis of ent-kauranoids by the pig liver esterase-catalyzed asymmetric hydrolysis of a dialkyl malonate-type prochiral diester

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• 作者：Yuji Namiki ; Tomohiro Fujii ; Masahisa Nakada ; ^{mnakada@waseda.jp" class="auth_mail}
• 刊名：Tetrahedron: Asymmetry
• 出版年：15 May 2014
• 年：2014
• 卷：25
• 期：9
• 页码：718-724
• 全文大小：1120 K

文摘

The preparation of chiral building blocks, suitable for use in the enantioselective total synthesis of kauranoids and ent-kauranoids, is reported herein. The pig liver esterase-catalyzed asymmetric hydrolysis of dimethyl 3,3-dimethyl-2-methylenecyclohexane-1,2-dicarboxylate, a malonate-type prochiral diester, afforded the corresponding half-ester in 96% yield and with 99% enantiomeric excess. The absolute configuration of the half-ester was determined by X-ray crystallographic analysis of its derivative and its enantiodivergent transformations are also described herein.