DIASTEREOSELECTIVE SYNTHESIS OF PROTECTED SYN 1,3-DIOLS BY BASE-CATALYZED INTRAMOLECULAR CONJUGATE ADDITION OF HEMIACETAL-DERIVED ALKOXIDE NUCLEOPHILES

被引：173

作者：

EVANS, DA

GAUCHETPRUNET, JA

机构：

[1] Department of Chemistry, Harvard University, Cambridge

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 09期

关键词：

D O I：

10.1021/jo00061a018

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of the illustrated unsaturated hydroxy esters (X = OMe, R2 = H, Me) and amides (X = N(Me)OMe, R2 = H, Me) with benzaldehyde and potassium alkoxide or amide bases is reported. The resulting benzylidene acetals are obtained in good yields (71-84%) and with high selectivity (>90: 10). In addition to an exploration of the scope of the reaction, a mechanistic study, involving the use of deuterated benzaldehyde to ascertain the rate-determining step of the process, is described.

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页码：2446 / 2453

页数：8

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