155395-70-3Relevant articles and documents
Chiral bicyclic lactams as homoenolate equivalents: An asymmetric route to 5-substituted cyclohexenones
Schwarz, Jacob B.,Devine, Paul N.,Meyers
, p. 8795 - 8806 (1997)
Bicyclic Lactam 2 was transformed info α-cyanoenamine 8 in a four- step, high-yielding process. γ-Metalation of 8 was achieved using LiTMP in THF/HMPA, and the resultant homoenolate equivalent underwent stereoselective alkylation and subsequent hydrolysis to provide lactams of type 10 as a single diasteraomer. Partial reduction and hydrolysis of lactams 10 furnished enantiopure 5-substituted cyclohexenones 13 in good overall yield.