用于制备取代的1,2 - 二胺的催化C-H胺化反应。
Catalytic C-H amination for the preparation of substituted 1,2-diamines.
作者信息
Olson David E, Du Bois J
机构信息
Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA.
出版信息
J Am Chem Soc. 2008 Aug 27;130(34):11248-9. doi: 10.1021/ja803344v. Epub 2008 Aug 5.
Abstract
Rhodium-catalyzed C-H insertion of hydroxylamine-derived sulfamate esters makes possible the synthesis of unique oxathiadiazinane heterocycles, which upon mild reduction furnish differentially substituted 1,2-diamine products. This highly chemo- and diastereoselective transformation underscores the power of catalytic C-H functionalization as a general approach to C-N bond construction.
摘要
铑催化的羟胺衍生氨基磺酸酯的C-H插入反应使得独特的氧杂硫二氮杂环烷杂环化合物的合成成为可能，这些杂环化合物经温和还原后可提供不同取代的1,2-二胺产物。这种高度化学选择性和非对映选择性的转化突出了催化C-H官能化作为构建C-N键的通用方法的强大功能。
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本文引用的文献
1
The Chemistry of Vicinal Diamines.邻二胺的化学
Angew Chem Int Ed Engl. 1998 Oct 16;37(19):2580-2627. doi: 10.1002/(SICI)1521-3773(19981016)37:19<2580::AID-ANIE2580>3.0.CO;2-L.
2
A diastereo- and enantioselective synthesis of alpha-substituted syn-alpha,beta-diamino acids.α-取代的顺式α,β-二氨基酸的非对映选择性和对映选择性合成。
J Am Chem Soc. 2008 May 7;130(18):5866-7. doi: 10.1021/ja8011808. Epub 2008 Apr 15.
3
Cobalt dinitrosoalkane complexes in the C-H functionalization of olefins.钴二亚硝基烷烃配合物在烯烃的C-H官能化反应中。
J Am Chem Soc. 2008 Mar 26;130(12):3777-9. doi: 10.1021/ja800738d. Epub 2008 Mar 5.
4
Cu(I)-catalyzed cycloguanidination of olefins.铜（I）催化的烯烃环胍化反应。
Org Lett. 2008 Mar 20;10(6):1087-90. doi: 10.1021/ol702974s. Epub 2008 Feb 27.
5
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
Cu(I)-catalyzed intermolecular diamination of activated terminal olefins.铜（I）催化的活性末端烯烃的分子间双胺化反应。
Org Lett. 2007 Nov 22;9(24):4943-5. doi: 10.1021/ol702061s. Epub 2007 Nov 1.
7
Direct catalytic enantioselective Mannich reactions: synthesis of protected anti-alpha,beta-diamino acids.直接催化对映选择性曼尼希反应：受保护的反式α,β-二氨基酸的合成
J Am Chem Soc. 2007 Sep 5;129(35):10632-3. doi: 10.1021/ja073473f. Epub 2007 Aug 11.
8
A Pd(0)-catalyzed diamination of terminal olefins at allylic and homoallylic carbons via formal C-H activation under solvent-free conditions.在无溶剂条件下，通过形式上的C-H活化，实现Pd(0)催化的末端烯烃在烯丙基和高烯丙基碳上的双胺化反应。
J Am Chem Soc. 2007 Jun 20;129(24):7496-7. doi: 10.1021/ja072080d. Epub 2007 May 24.
9
Copper(II) carboxylate promoted intramolecular diamination of terminal alkenes: improved reaction conditions and expanded substrate scope.羧酸铜（II）促进的末端烯烃分子内双胺化反应：改进的反应条件及扩大的底物范围
Org Lett. 2007 May 10;9(10):2035-8. doi: 10.1021/ol0706713. Epub 2007 Apr 21.
10
Stereocontrolled route to vicinal diamines by [3.3] sigmatropic rearrangement of allyl cyanate: asymmetric synthesis of anti-(2R,3R)- and syn-(2R,3S)-2,3-diaminobutanoic acids.通过异氰酸烯丙酯的[3.3]σ迁移重排立体控制合成邻二胺：抗-(2R,3R)-和顺-(2R,3S)-2,3-二氨基丁酸的不对称合成。
Org Lett. 2006 Dec 7;8(25):5737-40. doi: 10.1021/ol0621102.
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