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
收藏
页码：4132 / 4135
页数：4
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