Stratingh Institute for Chemistry , University of Groningen , Nijenborgh 4 , 9747 AG Groningen , The Netherlands.
Institute of Materials Research and Engineering , 2 Fusionopolis Way, Innovis #08-03 , Singapore 138634.
J Am Chem Soc. 2018 Jun 13;140(23):7052-7055. doi: 10.1021/jacs.8b02992. Epub 2018 May 31.
The highly regio- and enantioselective (up to >99:1 dr, up to 99:1 er) desymmetrization of meso-1,4-dibromocycloalk-2-enes using asymmetric allylic substitution with organolithium reagents to afford enantioenriched bromocycloalkenes (ring size of 5 to 7) has been achieved. The cycloheptene products undergo an unusual ring contraction. The synthetic versatility of this Cu(I)-catalyzed reaction is demonstrated by the concise stereocontrolled preparation of cyclic amino alcohols, which are privileged chiral structures in natural products and pharmaceuticals and widely used in synthesis and catalysis.
使用不对称烯丙基取代反应，通过有机锂试剂对消旋的 1,4-二溴环烷-2-烯进行高区域和对映选择性（高达 >99:1 dr，高达 99:1 er）去对称化，得到手性富集的溴环烷烯（环大小为 5 到 7）。环庚烯产物经历了不寻常的环收缩。Cu(I)催化反应的合成多功能性通过简洁的立体控制制备环状氨基醇得到证明，环状氨基醇在天然产物和药物中是具有特权的手性结构，并且广泛用于合成和催化。
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