Asymmetric [3+2] Cycloaddition of 2,2 '-Diester Aziridines To Synthesize Pyrrolidine Derivatives

作者：Liao, Yuting; Zhou, Baixin; Xia, Yong; Liu, Xiaohua^*; Lin, Lili; Feng, Xiaoming^*

来源：ACS Catalysis, 2017, 7(6): 3934-3939.

DOI：10.1021/acscatal.7b00787

• asymmetric cycloaddition
• 2,2 '-diester aziridines
• 3,4-dihydropyrans
• dysprosium
• octahydropyrano[2,3-c]pyrroles

A highly diastereo- and enantioselective [3 + 2] cycloaddition of 2,2'-diester aziridines with 3,4-dihydropyran derivatives and acyclic enol ethers has been established. Various optically active octahydropyrano[2,3-c]pyrrole and 3methoxypyrrolidine derivatives were generated in moderate to high yields (up to 94%) and good stereoselectivities (>19:1 dr, up to 95.5:4.5 er). The methodology was also applied in the highly diastereoselective synthesis of D-galactal derivatives. The absolute configuration of the octahydropyrano[2,3-c]pyrroles showed that the reactions using 3,4-dihydropyran and 6-alkyl-substituted ones as substrates gave reversed diastereoselection in the final cyclization step.

• 出版日期2017-6
• 单位四川大学