Enantioselective One-Pot Conjugate Addition of Grignard Reagents to Cyclic Enones Followed by Amidomethylation

被引：16

作者：

Bilcik, Filip ^{[1
]}

Drusan, Michal ^{[1
]}

Marak, Jozef ^{[2
]}

Sebesta, Radovan ^{[1
]}

机构：

[1] Comenius Univ, Fac Nat Sci, Dept Organ Chem, SK-84215 Bratislava, Slovakia

[2] Comenius Univ, Fac Nat Sci, Dept Analyt Chem, SK-84215 Bratislava, Slovakia

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 01期

关键词：

TANDEM 1,4-ADDITION-ALDOL REACTION; ASYMMETRIC-SYNTHESIS; ELECTROPHILES; 4-ISOPROPYL-5,5-DIPHENYLOXAZOLIDIN-2-ONE; AUXILIARY; CATALYSIS; EFFICIENT; CENTERS; LIGANDS;

D O I：

10.1021/jo202146f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantioselective conjugate addition of Grignard reagents to enones, catalyzed by Cu-Taniaphos or Josiphos complex, affords chiral enolates. Ensuing one-pot Mannich reaction with TiCl4-generated imine leads to aminocarbonyl compounds with benzyloxycarbonyl-protected nitrogen. Both diastereomers of these compounds are isolated in moderate yields but high enantiomeric purities (up to er 97.5:2.5).

引用

页码：760 / 765

页数：6

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