Diastereoselective trimolecular condensation between indole, Meldrum's acid and chiral sugar-derived aldehydes

被引：10

作者：

Dardennes, Emmanuel ^{[1
,2
]}

Gerard, Stephane ^{[1
]}

Petermann, Christian ^{[1
]}

Sapi, Janos ^{[1
]}

机构：

[1] Univ Reims, ICMR, CNRS, UMR 6229,Grp BSMA,UFR Pharm, F-51096 Reims, France

[2] Sygnature Chem Serv, Nottingham NG1 1GF, England

来源：

TETRAHEDRON-ASYMMETRY | 2010年 / 21卷 / 02期

关键词：

ASYMMETRIC MULTICOMPONENT REACTIONS; TANDEM;

D O I：

10.1016/j.tetasy.2009.12.017

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The trimolecular condensation of indole, Meldrum's acid and chiral, sugar-derived aldehydes took place in good yield and high diastereoselectivity. The absolute configuration of the alpha-carbon of the chiral aldehydes ensured a predictable diastereocontrol of the newly created stereogenic centre except for (3aR,5S,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydrofuro[3,2-d][1,3]dioxole-5-carbaldehyde 3i. In this case, the opposite stereochemistry may be explained by a less congested conformer of the Knoevenagel-adduct intermediate. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：208 / 215

页数：8

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