Highly selective cascade couplings for the syntheses of functionalized piperidinones and bispidines.
Efficient cascade couplings to synthesize functionalized piperidinones 1 and bispidines 2 and 3 have been developed. Simple modifications to the reaction conditions allow for the highly controlled and selective formation of each compound. In addition, the cis isomer of 1 can be selectively obtained under acidic conditions, while the preparation of the corresponding trans isomer can also be readily realized through a base-catalyzed, dynamic crystallization-driven process.
Xu
Feng
F
Department of Process Research, Merck Research Laboratories, Rahway, NJ 07065, USA. feng_xu@merck.com
Corley
Edward
E
Murry
Jerry A
JA
Tschaen
David M
DM
D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis*; D003460:Crystallization; D007202:Indicators and Reagents; D008968:Molecular Conformation; D004364:Pharmaceutical Preparations / Q000138:chemical synthesis; D010880:Piperidines / Q000138:chemical synthesis*; D013237:Stereoisomerism
D019086:Bridged Bicyclo Compounds, Heterocyclic; D007202:Indicators and Reagents; D004364:Pharmaceutical Preparations; D010880:Piperidines; C495809:bispidine