One-Pot Preparation of Chiral Carbacycles from Morita-Baylis-Hillman Carbonates by an Asymmetric Allylic Alkylation/Olefin Metathesis Sequence

被引：8

作者：

Putaj, Piotr ^{[1
]}

Ticha, Iveta ^{[1
]}

Cisarova, Ivana ^{[2
]}

Vesely, Jan ^{[1
]}

机构：

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

[2] Charles Univ Prague, Fac Sci, Dept Inorgan Chem, Prague 12843 2, Czech Republic

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 2014卷 / 30期

关键词：

Organocatalysis; Asymmetric synthesis; Morita-Baylis-Hillman carbonates; Metathesis; MBH CARBONATES; ORGANOCATALYTIC SYNTHESIS; 3+2 ANNULATION; CONSTRUCTION; FUNCTIONALIZATION; SUBSTITUTION; DIASTEREO; LIGANDS; CASCADE; REGIO;

D O I：

10.1002/ejoc.201402899

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An operationally simple, one-pot synthetic protocol for the formation of all-carbon, highly substituted five- and six-membered rings is described. In this two-step procedure, an asymmetric allylic alkylation (AAA) of Morita-Baylis-Hillman (MBH) carbonates with allylmalononitrile, catalyzed by a chiral tertiary amine, is followed by a ring-closing alkene metathesis (RCM) reaction. Products are obtained in high yields, and an excellent level of optical purity of some of the target compounds is achieved after just a single recrystallization.

引用

页码：6615 / 6620

页数：6

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