STEREOSELECTIVE TITANIUM-MEDIATED ALDOL REACTIONS OF MENTHYL ACETATE ENOLATES, AND ALLYLATIONS WITH BENZALDEHYDE

被引：7

作者：

CAMBIE, RC ^{[1
]}

CODDINGTON, JM ^{[1
]}

MILBANK, JBJ ^{[1
]}

PAUSLER, MG ^{[1
]}

RUSTENHOVEN, JJ ^{[1
]}

RUTLEDGE, PS ^{[1
]}

SHAW, GL ^{[1
]}

SINKOVICH, PI ^{[1
]}

机构：

[1] UNIV AUCKLAND,DEPT CHEM,AUCKLAND,NEW ZEALAND

来源：

AUSTRALIAN JOURNAL OF CHEMISTRY | 1993年 / 46卷 / 05期

关键词：

D O I：

10.1071/CH9930583

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The enolates of (+)- and (-)-menthyl acetate, formed by transmetallation from lithium with chloro(cyclopentadienyl)bis(1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranosato-O3)titaniUM [CpTi(DAGO)2Cl] (1), react with benzaldehyde from the Re-face with high stereoselectivities (95 and 92% diastereomeric excess) when 12-crown-4 is used during the transmetallation. Use of the chiral cyclopentadienyltitanium-alpha,alpha,alpha',alpha'-tetraaryl-2,2-dimethyl-1,3-dioxolan-4,5-dimethanol (TADDOL) complex (3) gives lower diastereoselectivities (58 and 40%) but the Si-face of benzaldehyde is attacked preferentially. Transmetallation of the 2-methylprop-2-enyl moiety to CpTi(DAGO)2Cl gives an allyltitanium reagent (2) which reacts with benzaldehyde from the Re-face with 88% enantiomeric excess.

引用

页码：583 / 591

页数：9

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