Evaluation of an aza-Michael approach for the synthesis of 3,3-dimethyl-2-aminocyclobutane-1-carboxylic acid

被引：5

作者：

Charnay-Pouget, Florence ^{[1
]}

Frank, Michael ^{[2
]}

Baltaze, Jean-Pierre ^{[1
]}

Pereira, Elisabeth ^{[2
]}

Aitken, David J. ^{[1
]}

机构：

[1] Univ Paris 11, CNRS, ICMMO, UMR 8182, 15 Rue Georges Clemenceau, F-91405 Orsay, France

[2] Univ Blaise Pascal, Clermont Univ, CNRS, Lab SEESIB,UMR 6504, F-63177 Clermont Ferrand, France

来源：

ARKIVOC | 2012年

关键词：

Aza-Michael reaction; cyclobutenecarboxylate; beta-amino acid; conjugate addition; BETA-AMINO ACIDS; PARALLEL KINETIC RESOLUTION; HELICAL SECONDARY STRUCTURE; ASYMMETRIC-SYNTHESIS; CONJUGATE ADDITION; LITHIUM AMIDES; SIDE-CHAINS; PEPTIDES; CHEMISTRY; 3-ALKYL-CISPENTACIN;

D O I：

10.3998/ark.5550190.0013.509

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The aza-Michael addition reaction of a dibenzylic amide anion with t-butyl 3,3-dimethylcyclobutene-1-carboxylate was investigated as a route to the title compound, a cyclic beta-amino acid. In analogy with the known 5- and 6-membered ring homologues, the addition reaction proceeds smoothly, but with moderate diastereomeric and enantiomeric selectivities. The trans isomer of the title beta-amino acid was obtained, for the first time, with a modest enantiomeric excess.

引用

页码：80 / 93

页数：14

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