Cycloalkene Carbonitriles in Rhodium-Catalyzed 1,4-Addition and Formal Synthesis of Vabicaserin.
Cycloalkenes with exocyclic acceptor substituents still remain challenging substrates for enantioselective rhodium-catalyzed 1,4-addition. Cycloalkene 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.
Leibniz University of Hannover , Institute of Organic Chemistry, Schneiderberg 1B, D-30167 Hannover, Germany.
Wojciech J
WJ
Dziechciejewski
Leibniz University of Hannover , Institute of Organic Chemistry, Schneiderberg 1B, D-30167 Hannover, Germany.
Regina
R
Weber
Leibniz University of Hannover , Institute of Organic Chemistry, Schneiderberg 1B, D-30167 Hannover, Germany.
Oliver
O
Sowada
Leibniz University of Hannover , Institute of Organic Chemistry, Schneiderberg 1B, D-30167 Hannover, Germany.
Mike M K
MM
Boysen
D003516:Cycloparaffins / Q000737:chemistry*; D003517:Cyclopentanes / Q000737:chemistry; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
D003516:Cycloparaffins; D003517:Cyclopentanes; D006576:Heterocyclic Compounds, 4 or More Rings; D012238:Rhodium; C556517:vabicaserin