Lewis Base Catalyzed Enantioselective Allylation of α,β-Unsaturated Aldehydes

被引：45

作者：

Kadlcikova, Aneta ^{[1
]}

Valterova, Irena ^{[2
]}

Duchackova, Lucie ^{[1
]}

Roithova, Jana ^{[1
]}

Kotora, Martin ^{[1
,2
]}

机构：

[1] Charles Univ Prague, Dept Organ & Nucl Chem, Fac Sci, Prague 12843 2, Czech Republic

[2] Acad Sci Czech Republ, Inst Organ Chem & Biochem, Prague 16610 6, Czech Republic

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2010年 / 16卷 / 31期

关键词：

allylation; asymmetric synthesis; lewis bases; organocatalysis; nitrogen oxides; ATROPOISOMERIC BIPYRIDINE N; N'-DIOXIDES; PYRIDINE N-OXIDES; ASYMMETRIC ALLYLATION; ALLYLTRICHLOROSILANE; ORGANOCATALYSTS; REAGENTS; LIGANDS; PATHWAY; ROUTE;

D O I：

10.1002/chem.201001523

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Being selective: The catalytic allylation of, α,β-unsaturated aldehydes with allyltrichlorosilane in the presence of chiral 3,3′-unsymmetrically substituted bis(tetrahydroisoquinoline) N,N-dioxides was explored. The allylation of various aldehydes proceeded under mild reaction conditions (-78□ °C) with high yields and enantioselectivity (see scheme). This allylation was applied in the synthesis of (S)-(-)-goniothalamin. © 2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：9442 / 9445

页数：4

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