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本文引用的文献

1
Asymmetric copper-catalysed intramolecular C-H insertion reactions of α-diazo-β-keto sulfones.不对称铜催化的α-重氮-β-酮亚砜的分子内 C-H 插入反应。
Org Biomol Chem. 2011 Feb 7;9(3):667-9. doi: 10.1039/c0ob00914h. Epub 2010 Nov 30.
2
Formation of six- vs. five-membered cyclic sulfones by C-H insertion.通过C-H插入形成六元与五元环状砜。
Tetrahedron Lett. 2009 Apr 29;50(17):1954-1957. doi: 10.1016/j.tetlet.2009.02.044.
3
Highly enantioselective intramolecular copper catalyzed C-H insertion reactions of alpha-diazosulfones.高对映选择性的铜催化α-重氮砜的分子内 C-H 插入反应。
J Am Chem Soc. 2010 Feb 3;132(4):1184-5. doi: 10.1021/ja909713a.
4
Probing the importance of the hemilabile site of bis(phosphine) monoxide ligands in the copper-catalyzed addition of diethylzinc to N-phosphinoylimines: discovery of new effective chiral ligands.探究单氧化双（膦）配体的半不稳定位点在铜催化二乙基锌加成到N-磷酰亚胺反应中的重要性：新型有效手性配体的发现
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Catalytic C-H functionalization by metal carbenoid and nitrenoid insertion.通过金属卡宾体和氮宾体插入实现的催化C-H官能团化。
Nature. 2008 Jan 24;451(7177):417-24. doi: 10.1038/nature06485.
6
Delta-sultone formation through Rh-catalyzed C-H insertion.通过铑催化的C-H插入反应形成δ-磺内酯。
Org Lett. 2007 Oct 11;9(21):4363-6. doi: 10.1021/ol701950d. Epub 2007 Sep 21.
7
Selective formation of six-membered cyclic sulfones and sulfonates by C-H insertion.
Org Lett. 2007 Jan 4;9(1):61-3. doi: 10.1021/ol062592h.
8
Dirhodium tetracarboxylate derived from adamantylglycine as a chiral catalyst for carbenoid reactions.源自金刚烷甘氨酸的四羧基二铑作为卡宾反应的手性催化剂。
Org Lett. 2006 Aug 3;8(16):3437-40. doi: 10.1021/ol060893l.

通过铑（II）催化的C-H插入过程实现新木脂素（-）-表-conocarpan和（+）-conocarpan的不对称合成以及（-）-表-conocarpan绝对构型的修正。

Asymmetric synthesis of neolignans (-)-epi-conocarpan and (+)-conocarpan via Rh(II)-catalyzed C-H insertion process and revision of the absolute configuration of (-)-epi-conocarpan.

作者信息

Natori Yoshihiro, Tsutsui Hideyuki, Sato Naoki, Nakamura Seiichi, Nambu Hisanori, Shiro Motoo, Hashimoto Shunichi

机构信息

Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan.

出版信息

J Org Chem. 2009 Jun 5;74(11):4418-21. doi: 10.1021/jo900502d.

DOI:10.1021/jo900502d
PMID:19408907
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3541823/
Abstract

Catalytic asymmetric synthesis of neolignan natural products (-)-epi-conocarpan and (+)-conocarpan has been achieved by exploiting an enantio- and diastereoselective intramolecular C-H insertion reaction to construct a cis-2-aryl-2,3-dihydrobenzofuran ring system as a key step. The C-H insertion reaction of 5-bromoaryldiazoacetate catalyzed by Rh(2)(S-PTTEA)(4), a new dirhodium(II) carboxylate complex that incorporates N-phthaloyl-(S)-triethylalaninate as chiral bridging ligands, provided 2-aryl-5-bromo-3-methoxycarbonyl-2,3-dihydrobenzofuran with exceptionally high diastereoselectivity (cis/trans = 97:3) and high enantioselectivity for the cis isomer (84% ee).

摘要

通过利用对映和非对映选择性分子内C-H插入反应构建顺式-2-芳基-2,3-二氢苯并呋喃环系统作为关键步骤，实现了新木脂素天然产物（-）-表松柏醇和（+）-松柏醇的催化不对称合成。由新型二铑（II）羧酸盐配合物Rh(2)(S-PTTEA)(4)催化的5-溴芳基重氮乙酸酯的C-H插入反应，该配合物包含N-邻苯二甲酰基-（S）-三乙丙氨酸作为手性桥连配体，以极高的非对映选择性（顺式/反式=97:3）和顺式异构体的高对映选择性（84% ee）提供了2-芳基-5-溴-3-甲氧基羰基-2,3-二氢苯并呋喃。