1005772-83-7Relevant academic research and scientific papers
Enantioselective, NHC-catalyzed bicyclo-β-lactam formation via direct annulations of enals and unsaturated N-sulfonyl ketimines
He, Ming,Bode, Jeffrey W.
, p. 418 - 419 (2008)
A wide range of α,β-unsaturated aldehydes, including 3-alkyl derivatives, undergo N-heterocyclic carbene (NHC)-catalyzed annulations with N-sulfonyl ketimines under mild conditions to provide bicyclo[3.2.0]lactams with outstanding diastereo- and enantioselectivity. This concise route to β-lactams established four new chiral centers in a single operation. Although this process could occur via the intermediacy of a catalytically generated homoenolate equivalent, the stereochemical outcome supports a tandem or concerted aza-Benzoin/oxy-Cope reaction as the key bond-forming step. Copyright
