Double Bond Isomerization/Enantioselective Aza-Petasis-Ferrier Rearrangement Sequence as an Efficient Entry to Anti- and Enantioenriched β-Amino Aldehydes

被引：129

作者：

Terada, Masahiro ^{[1
]}

Toda, Yasunori ^{[1
]}

机构：

[1] Tohoku Univ, Grad Sch Sci, Dept Chem, Sendai, Miyagi 9808578, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2009年 / 131卷 / 18期

关键词：

CHIRAL BRONSTED ACID; MANNICH REACTIONS; CATALYSIS; ACTIVATION; IMINES; ETHERS;

D O I：

10.1021/ja902202g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Highly anti- and enantioselective synthesis of beta-amino aldehydes having an aliphatic substituent. at the beta-position was accomplished by a combination of two catalytic reactions, that is, an initial Ni(II) complex-catalyzed isomerization of a double bond followed by a chiral phosphoric acid catalyzed aza-Petasis-Ferrier rearrangement, using hemiaminal allyl ethers as the initial substrate. The chiral phosphoric acid also functioned as an efficient resolving catalyst of racemic hemiaminal vinyl ethers.

引用

页码：6354 / +

页数：3

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