Structural optimization of thiourea-based bifunctional organocatalysts for the highly enantioselective dynamic kinetic resolution of azlactones

被引：99

作者：

Berkessel, Albrecht ^{[1
]}

Mukherjee, Santanu ^{[1
]}

Mueller, Thomas N. ^{[1
]}

Cleemann, Felix ^{[1
]}

Roland, Katrin ^{[1
]}

Brandenburg, Marc ^{[1
]}

Neudoerfl, Joerg-M. ^{[1
]}

Lex, Johann ^{[1
]}

机构：

[1] Univ Cologne, Inst Organ Chem, D-50939 Cologne, Germany

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2006年 / 4卷 / 23期

关键词：

D O I：

10.1039/b607574f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This article describes the synthesis of a library of structurally diverse bifunctional organocatalysts bearing both a quasi-Lewis acidic (thio) urea moiety and a Bronsted basic tertiary amine group. Sequential modi. cation of the modular catalyst structure and subsequent screening of the compounds in the alcoholytic dynamic kinetic resolution (DKR) of azlactones revealed valuable structure-activity relationships. In particular, a "hit-structure" was identified which provides e. g. N-benzoyl-tert-leucine allyl ester in an excellent enantiomeric excess of 95%.

引用

页码：4319 / 4330

页数：12

共 57 条

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