New S, O-acetals from (1R)-(−)-myrtenal as chiral auxiliaries in nucleophilic additions

…, S Pérez-Estrada, ME Vargas-Dı́az, P Joseph-Nathan…

Index: Chacon-Garcia, Luis; Lagunas-Rivera, Selene; Perez-Estrada, Salvador; Vargas-Diaz, M. Elena; Joseph-Nathan, Pedro; Tamariz, Joaquin; Zepeda, L. Gerardo Tetrahedron Letters, 2004 , vol. 45, # 10 p. 2141 - 2145

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Citation Number: 16

Abstract

Treatment of hydroxythiol with α, α-diethoxyacetophenone at room temperature yielded a mixture of epimeric S, O-acetals and (1: 4, 92% yield), which were efficiently separated by flash chromatography. The OTBS derivatives and were treated with several Grignard reagents to afford carbinols and respectively (85–99% yield,> 95% dr). After successive hydrolysis and reduction of 10 and 13 it is possible to obtain either enantiomer of diols in ...