Enantio- and Diastereoselective Organocatalytic α-Alkylation of Aldehydes with 3-Substituted 2-(Bromomethyl)acrylates

被引：15

作者：

Jimenez, Jacqueline ^{[1
]}

Landa, Aitor ^{[1
]}

Lizarraga, Aitziber ^{[1
]}

Maestro, Miguel ^{[1
]}

Mielgo, Antonia ^{[1
]}

Oiarbide, Mikel ^{[1
]}

Velilla, Irene ^{[1
]}

Palomo, Claudio ^{[1
]}

机构：

[1] Univ Basque Country, Fac Quim, Dept Quim Organ 1, San Sebastian 20080, Spain

来源：

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

关键词：

TRANSITION-METAL; ENANTIOSELECTIVE CYCLOPROPANATION; ASYMMETRIC ALKYLATION; GAMMA-ALKYLATION; CATALYSIS; ALLYLATION; ARYLATION; CASCADE;

D O I：

10.1021/jo202073n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The catalytic direct alpha-alkylation of aldehydes with 2-(bromomethyl)acrylates has been accomplished, giving rise to alpha-branched and functionalized aldehydes of high diastereo- and enantiopurity. The influence of the nature of the ester group of the acrylates in reaction stereoselectivity and especially in reactivity is investigated. Optimum conditions implicate the use of phenyl acrylates in conjunction with organocatalyst 8. Application of thus obtained adducts in synthesis is illustrated with a concise stereocontrolled preparation of trisubstituted cyclopentenes.

引用

页码：747 / 753

页数：7

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