Catalytic asymmetric synthesis of (-)-E-δ-viniferin via an intramolecular C-H insertion of diaryldiazomethane using Rh2(S-TFPTTL)4
Catalytic asymmetric synthesis of (-)-E-δ-viniferin via an intramolecular C-H insertion of diaryldiazomethane using Rh2(S-TFPTTL)4
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DOI：
10.1016/j.tetlet.2015.05.072
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发表时间：
2015-07-15
影响因子：
1.8
通讯作者：
Hashimoto, Shunichi
中科院分区：
文献类型：
--
作者：
Natori, Yoshihiro;Ito, Motoki;Hashimoto, Shunichi
以Rh(II)催化的二芳基重氮甲烷衍生物的分子内C-H插入反应为关键步骤，实现了反式白藜芦醇二聚体的不对称合成。2，3-二芳基-2，3-二氢苯并呋喃的2，3-二芳基-2，3-二氢苯并呋喃在tetrakis[N-tetrafluorophthaloyl-(S)-tert-leucinate]，Rh-2(4)催化下的C-H插入反应提供了良好的顺式非对映选择性和96%的ee。(C)2015爱思唯尔有限公司。保留所有权利。
An asymmetric synthesis of (-)-E-delta-viniferin, a trans-resveratrol dimer natural product containing a dihydrobenzofuran ring, has been achieved by exploiting a Rh(II)-catalyzed intramolecular C-H insertion reaction of a diaryldiazomethane derivative as a key step. The C-H insertion under catalysis by dirhodium(II) tetrakis[N-tetrafluorophthaloyl-(S)-tert-leucinate], Rh-2(S-TFPTTL)(4), provided the 2,3-diaryl-2,3-dihydrobenzofuran core structure with perfect cis diastereoselectivity and 96% ee. (c) 2015 Elsevier Ltd. All rights reserved.