Tetrahedron

Alkyl 2-(2-benzothiazolylsulfinyl) acetates as useful synthetic reagents for alkyl 4-hydroxyalk-2-enoates by sulfinyl-Knoevenagel reaction

Z Du, T Kawatani, K Kataoka, R Omatsu, J Nokami

Index: Du, Zhenjun; Kawatani, Toshihiro; Kataoka, Kazuhide; Omatsu, Rikiya; Nokami, Junzo Tetrahedron, 2012 , vol. 68, # 11 p. 2471 - 2480

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Abstract

Isopropyl, ethyl, and methyl 2-(2-benzothiazolylsulfinyl) acetates have been found to be useful synthetic reagents for sulfinyl-Knoevenagel reaction with various aldehydes to give directly the corresponding 4-hydroxyalk-2-enoates [R′ CH (OH) CHCHCO2R], which are ubiquitous structures in biologically active natural products and useful building blocks for organic synthesis of chiral compounds. From the optically pure (R)-2-(2- ...