Title of article
New S,O-acetals from (1R)-(−)-myrtenal as chiral auxiliaries in nucleophilic additions
Author/Authors
Chac?n-Garc??a، نويسنده , , Luis and Lagunas-Rivera، نويسنده , , Selene and Pérez-Estrada، نويسنده , , Salvador and Elena Vargas-D??az، نويسنده , , M. and Joseph-Nathan، نويسنده , , Pedro and Tamariz، نويسنده , , Joaqu??n and Zepeda، نويسنده , , L.Gerardo، نويسنده ,
Issue Information
هفته نامه با شماره پیاپی سال 2004
Pages
5
From page
2141
To page
2145
Abstract
Treatment of hydroxythiol 4 with α,α-diethoxyacetophenone at room temperature yielded a mixture of epimeric S,O-acetals 6 and 7 (1:4, 92% yield), which were efficiently separated by flash chromatography. The OTBS derivatives 8 and 9 were treated with several Grignard reagents to afford carbinols 10 and 13 respectively (85–99% yield, >95% dr). After successive hydrolysis and reduction of 10 and 13 it is possible to obtain either enantiomer of diols 16 in high optical purity (>95% er).
Keywords
S , 2-diols , (1R)-(?)-Myrtenal , O-acetals , Chiral 1 , Diastereoselective nucleophilic additions
Journal title
Tetrahedron Letters
Serial Year
2004
Journal title
Tetrahedron Letters
Record number
1657464
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