Regio- and Stereoselective Approach to 1,4-Ditertiary Carbinols from Dimethyl Tartrate

被引：3

作者：

Budragchaa, Tuvshinjargal ^{[1
]}

Roller, Alexander ^{[2
]}

Widhalm, Michael ^{[1
]}

机构：

[1] Univ Vienna, Fac Chem, Inst Organ Chem, A-1090 Vienna, Austria

[2] Univ Vienna, Fac Chem, Inst Inorgan Chem, A-1090 Vienna, Austria

来源：

SYNTHESIS-STUTTGART | 2012年 / 44卷 / 20期

关键词：

regioselectivity; diastereoselectivity; diols; nucleophilic addition; Grignard reaction; TARTARIC ACID; TADDOL ANALOGS; D-MANNITOL; LIGANDS; PHOSPHORAMIDITE; 1,4-DIKETONES; PHOSPHOLANES; DERIVATIVES; MONODENTATE; CATALYSIS;

D O I：

10.1055/s-0032-1317168

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A rational strategy for accessing tetrahydroxy compounds in predictable stereoselective fashion from di-O-benzyl protected tartrate is presented. Up to four different aromatic, aliphatic, and vinyl substituents could be stepwise introduced at C1 and C4. This is exemplified in an economic preparation of eight dihydroxy compounds from natural tartaric acid in six steps and 19-59% overall yield. A final deprotection step afforded the corresponding tetrahydroxy compounds in good yields.

引用

页码：3238 / 3250

页数：13

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