Improved protocol for asymmetric, intramolecular heteroatom Michael addition using organocatalysis: enantioselective syntheses of homoproline, pelletierine, and homopipecolic acid.
An improved protocol for the construction of enantioenriched pyrrolidine, indoline, and piperidine rings using an organocatalyzed, intramolecular heteroatom Michael addition is described. Application to the enantioselective synthesis of homoproline, homopipecolic acid, and pelletierine has been accomplished.
Department of Chemistry, 153 Gilbert Hall, Oregon State University, Corvallis, Oregon 97331, USA.
Erik C
EC
Carlson
Lauren K
LK
Rathbone
Hua
H
Yang
Nathan D
ND
Collett
Rich G
RG
Carter
D002384:Catalysis; D015394:Molecular Structure; D010875:Pipecolic Acids / Q000138:chemical synthesis*; D010880:Piperidines / Q000138:chemical synthesis*; D011392:Proline / Q000031:analogs & derivatives* / Q000138:chemical synthesis
D010875:Pipecolic Acids; D010880:Piperidines; C008195:isopelletierine; D011392:Proline; C010983:homoproline; C031345:pipecolic acid