Enantiopure bicyclic piperidinones: stereoselectivity in lactam enolate alkylations.
The synthesis and alkylation of [4.3.0]-bicyclic lactams, derived from 6-oxopipecolic acid, have been investigated. Alkylation can proceed with predominantly exo-diastereoselectivity, but the efficiency of this process depends on the substitution at the hemiaminal ether system. These products can be readily deprotected to give substituted hydroxymethyl lactams in good yield.
Brewster
Andrew G
AG
AstraZeneca Pharmaceuticals, Alderly Park, Macclesfield, UK.
Broady
Simon
S
Davies
Catherine E
CE
Heightman
Thomas D
TD
Hermitage
Stephen A
SA
Hughes
Mark
M
Moloney
Mark G
MG
Woods
Gordon
G