Enantio- and Diastereoselective Construction of Contiguous Tetrasubstituted Chiral Carbons in Organocatalytic Oxadecalin Synthesis
Enantio- and Diastereoselective Construction of Contiguous Tetrasubstituted Chiral Carbons in Organocatalytic Oxadecalin Synthesis
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DOI：
10.1021/acs.orglett.0c01501
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发表时间：
2020-06-19
期刊：
影响因子：
5.2
通讯作者：
Matsubara, Seijiro
中科院分区：
文献类型：
--
作者：
Wada, Yuuki;Murata, Ryuichi;Matsubara, Seijiro
开发了含 1,3-环己二酮的烯酮的有机催化对映和非对映选择性环醚化，涉及原位生成手性氰醇。这种转化为在稠环系统的桥头含有连续四取代手性碳的奥昔卡林衍生物提供了第一种催化不对称方法。根据取代基的不同，顺式和反式十氢化萘型支架均具有良好至优异的立体选择性，并且一系列官能团积累在反式十氢化萘衍生物的手性季碳部分上。
The organocatalytic enantio- and diastereoselective cycloetherification of 1,3-cyclohexanedione-bearing enones involving the in situ generation of chiral cyanohydrins was developed. This transformation offers the first catalytic asymmetric approach to oxadecalin derivatives containing contiguous tetrasubstituted chiral carbons at the bridge heads of the fused ring systems. Depending on substituents, both cis- and trans-decalin-type scaffolds were synthesized with good to excellent stereoselectivities, and a range of functional groups accumulated on the chiral quaternary carbon moieties of the trans-oxadecalin derivatives.