Cycloalkene Carbonitriles in Rhodium-Catalyzed 1,4-Addition and Formal Synthesis of Vabicaserin

被引：12

作者：

Dziechciejewski, Wojciech J. ^{[1
]}

Weber, Regina ^{[1
]}

Sowada, Oliver ^{[1
]}

Boysen, Mike M. K. ^{[1
]}

机构：

[1] Leibniz Univ Hannover, Inst Organ Chem, D-30167 Hannover, Germany

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 17期

关键词：

ARYLBORONIC ACIDS; ASYMMETRIC 1,4-ADDITION; 1,4-ADDITION/ENANTIOSELECTIVE PROTONATION; CONJUGATE ADDITION; STEREOCHEMISTRY; COMPLEXES; LIGANDS; KETONIZATION; IODINATION; ENONES;

D O I：

10.1021/acs.orglett.5b01849

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cycloalkenes with exocyclic acceptor substituents still remain challenging substrates for enantioselective rhodium-catalyzed 1,4-addition. Cyclo-alkene carbonitriles and carboxylates have been investigated, and a highly diastereo- and enantioselective protocol for 1,4-addition to cyclopentene and cycloheptene carbonitrile has been developed. This new asymmetric transformation was subsequently applied in the asymmetric formal synthesis of the drug candidate Vabicaserin.

引用

页码：4132 / 4135

页数：4

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