Asymmetric synthesis of 2-substituted piperidines using a multi-component coupling reaction: rapid assembly of (S)-coniine from (S)-1-(1-phenylethyl)-2-methyleneaziridine.
(S)-Coniine is made using a reaction which assembles the piperidine ring by the sequential formation of four new chemical bonds and installs the C-2 stereogenic centre with high levels of diastereocontrol (90% de).
Hayes
J F
JF
GlaxoSmithKline, Old Powder Mills, Tonbridge, Kent, UK TN11 9AN.
Shipman
M
M
Twin
H
H
D000470:Alkaloids / Q000138:chemical synthesis*; D001388:Aziridines / Q000737:chemistry*; D015394:Molecular Structure; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D010944:Plants / Q000737:chemistry; D013237:Stereoisomerism
C467816:1-(1-phenylethyl)-2-methyleneaziridine; D000470:Alkaloids; D001388:Aziridines; D010880:Piperidines; C007112:coniine