Tetrahedron

Enantioenriched synthesis of Escitalopram using lithiation–borylation methodology

BM Partridge, SP Thomas, VK Aggarwal

Index: Partridge, Benjamin M.; Thomas, Stephen P.; Aggarwal, Varinder K. Tetrahedron, 2011 , vol. 67, # 52 p. 10082 - 10088

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Citation Number: 5

Abstract

The asymmetric synthesis of Escitalopram has been completed using a lithiation–borylation reaction as the key step. Suitably functionalized enantioenriched carbamate (er 98: 2) and boronic ester coupling partners were prepared and following deprotonation with s-BuLi and borylation, the tertiary alcohol was obtained in 42% yield and 93: 7 er. The lithiation– borylation reaction was found to tolerate nitrile, benzylic alcohol and N-Boc functionalities. ...