Catalyst-controlled diastereoselective ring-opening formal [3+2]-cycloadditions of arylvinyl oxirane 2,2-diesters with cyclic N-sulfonyl imines
Catalyst-controlled diastereoselective ring-opening formal [3+2]-cycloadditions of arylvinyl oxirane 2,2-diesters with cyclic N-sulfonyl imines
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芳基乙烯基环氧乙烷2,2-二酯与环状N-磺酰亚胺的催化剂控制非对映选择性开环缩甲醛[3 2]-环加成反应
DOI：
10.1007/s11426-019-9760-7
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发表时间：
2020
期刊：
影响因子：
--
通讯作者：
Yang Hua
中科院分区：
文献类型：
--
作者：
Xiao Jun-An;Cheng Xiu-Liang;Peng Hai;Li Jin-Lian;Xie Zhen-Zhen;Chen Wen-Qiang;Liu Zhi-Ping;Xiao Qi;Su Wei;Yang Hua
本文报道了芳基乙烯基环氧乙烷2，2-二酯与环状N-磺酰亚胺的非对映选择性可控的[3+2]-环加成反应，在三氟甲磺酸钯（0）或钪（III）存在下，以中等至优异的产率和优异的非对映选择性得到相应的三环恶唑烷衍生物。该方案允许在可切换和温和的条件下选择性合成三环恶唑烷衍生物的非对映异构体。通过除去酯基和芳基乙烯基部分进行所得产物的进一步转化。
A diastereoselectivity-controllable formal [3+2]-cycloaddition of arylvinyl oxirane 2,2-diesters with cyclic N-sulfonyl imines is developed, affording the corresponding tricyclic oxazolidine derivatives in moderate to excellent yields with excellent diastereoselectivities in the presence of palladium(0) or scandium(III) triflate. This protocol allows selective synthesis of diastereomers of tricyclic oxazolidine derivatives under switchable and mild conditions. Further transformations of the obtained products were conducted by removing ester groups and arylvinyl moieties.