期刊
ACS CATALYSIS
卷 7, 期 6, 页码 3934-3939出版社
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.7b00787
关键词
asymmetric cycloaddition; 2,2 '-diester aziridines; 3,4-dihydropyrans; dysprosium; octahydropyrano[2,3-c]pyrroles
资金
- National Natural Science Foundation of China [21290182, 21572136]
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.
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