Synthesis of beta-Amino-Substituted Enones by Addition of Substituted Methyl Enones to Sulfinimines: Application to the Total Synthesis of Alkaloids (+)-Lasubine II and (+)-241D and the Formal Total Synthesis of (-)-Lasubine I

摘要

Addition of silyl enol ethers obtained from substituted methyl enones to chiral sulfinimines afforded the beta-amino-substituted enones with excellent selectivity. Utility of the obtained N-sulfinyl beta-amino ketones possessing a,alpha,beta-unsaturation is exemplified in the total synthesis of the quinolizidine alkaloid natural products (-)-lasubine I, (+)-lasubine II, and substituted piperidine alkaloid (+)-241-D.