Enantioselective synthesis of 1-alkyl-substituted 1-phenyl-1, 2-ethanediols using a myrtenal-derived chiral auxiliary

…, P Velázquez, J Tamariz, P Joseph-Nathan…

文献索引：Vargas-Diaz, Maria Elena; Chacon-Garcia, Luis; Velazquez, Pedro; Tamariz, Joaquin; Joseph-Nathan, Pedro; Zepeda, L. Gerardo Tetrahedron Asymmetry, 2003 , vol. 14, # 20 p. 3225 - 3232

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被引用次数: 25

摘要

The enantioselective synthesis of several 1-phenyl-1, 2-ethanodiol derivatives using 2- benzoyl-1, 3-oxathiane 1 as a chiral auxiliary is described. Nucleophilic additions of Grignard reagents, methyl lithium and LS-Selectride on benzoyloxathiane 1 proceeded in> 95% diastereomeric ratio (dr) affording the corresponding tertiary carbinols, which were successively hydrolyzed and reduced to give the title derivatives in> 95% enantiomeric ...