通过钯（0）催化末端烯烃的不对称烯丙基和高烯丙基C-H二胺化反应合成（+）-CP-99,994 。
Synthesis of (+)-CP-99,994 via Pd(0)-catalyzed asymmetric allylic and homoallylic C-H Diamination of terminal olefin.
作者信息
Fu Renzhong, Zhao Baoguo, Shi Yian
机构信息
Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA.
出版信息
J Org Chem. 2009 Oct 2;74(19):7577-80. doi: 10.1021/jo9015584.
Abstract
This paper describes an asymmetric synthesis of the potent substance P receptor antagonist (+)-CP-99,994 from 4-phenyl-1-butene via Pd(0)-catalyzed asymmetric allylic and homoallylic C-H diamination.
摘要
本文描述了通过钯（0）催化的不对称烯丙基和高烯丙基C-H双胺化反应，从4-苯基-1-丁烯不对称合成强效P物质受体拮抗剂（+）-CP-99,994。
相似文献
1
Synthesis of (+)-CP-99,994 via Pd(0)-catalyzed asymmetric allylic and homoallylic C-H Diamination of terminal olefin.
J Org Chem. 2009 Oct 2;74(19):7577-80. doi: 10.1021/jo9015584.
2
Catalytic asymmetric allylic and homoallylic diamination of terminal olefins via formal C-H activation.
J Am Chem Soc. 2008 Jul 9;130(27):8590-1. doi: 10.1021/ja8027394. Epub 2008 Jun 13.
3
Catalytic diamination of olefins via N-N bond activation.
Acc Chem Res. 2014 Dec 16;47(12):3665-78. doi: 10.1021/ar500344t. Epub 2014 Nov 17.
4
Transition-metal-catalyzed diamination of olefins.
Angew Chem Int Ed Engl. 2009;48(7):1190-3. doi: 10.1002/anie.200804362.
5
Cu(I)-catalyzed intermolecular diamination of activated terminal olefins.
Org Lett. 2007 Nov 22;9(24):4943-5. doi: 10.1021/ol702061s. Epub 2007 Nov 1.
6
Catalytic asymmetric diamination of conjugated dienes and triene.
J Am Chem Soc. 2007 Sep 26;129(38):11688-9. doi: 10.1021/ja074698t. Epub 2007 Sep 6.
7
A Cu/Pd Cooperative Catalysis for Enantioselective Allylboration of Alkenes.
J Am Chem Soc. 2015 Nov 4;137(43):13760-3. doi: 10.1021/jacs.5b09146. Epub 2015 Oct 22.
8
Enantioselective Allylic C-H Oxidation of Terminal Olefins to Isochromans by Palladium(II)/Chiral Sulfoxide Catalysis.
Angew Chem Int Ed Engl. 2016 Aug 8;55(33):9571-5. doi: 10.1002/anie.201603576. Epub 2016 Jul 4.
9
Pd-catalyzed asymmetric allylic alkylations of 3-substituted indoles using chiral P/olefin ligands.
Org Lett. 2013 Feb 15;15(4):740-3. doi: 10.1021/ol3032736. Epub 2013 Feb 7.
10
Pd(II)-Catalyzed Aminofluorination of Alkenes in Total Synthesis 6-(R)-Fluoroswainsonine and 5-(R)-Fluorofebrifugine.
Org Lett. 2016 Mar 4;18(5):960-3. doi: 10.1021/acs.orglett.6b00030. Epub 2016 Feb 16.
引用本文的文献
1
Enantioselective Synthesis of anti-1,2-Diamines by Cu-Catalyzed Reductive Couplings of Azadienes with Aldimines and Ketimines.
J Am Chem Soc. 2018 Jun 13;140(23):7083-7087. doi: 10.1021/jacs.8b04750. Epub 2018 May 30.
2
Catalytic diamination of olefins via N-N bond activation.
Acc Chem Res. 2014 Dec 16;47(12):3665-78. doi: 10.1021/ar500344t. Epub 2014 Nov 17.
3
Methods for direct alkene diamination, new & old.
Tetrahedron. 2012 Jun 3;68(22):4067-4105. doi: 10.1016/j.tet.2012.03.036. Epub 2012 Mar 21.
4
Cu(I)-catalyzed diamination of conjugated dienes. Complementary regioselectivity from two distinct mechanistic pathways involving Cu(II) and Cu(III) species.
J Am Chem Soc. 2011 Dec 28;133(51):20890-900. doi: 10.1021/ja207691a. Epub 2011 Dec 2.
5
Palladium(II)-catalyzed alkene functionalization via nucleopalladation: stereochemical pathways and enantioselective catalytic applications.
Chem Rev. 2011 Apr 13;111(4):2981-3019. doi: 10.1021/cr100371y. Epub 2011 Mar 23.
6
Modular Synthesis of 1,2-Diamine Derivatives via Palladium-Catalyzed Aerobic Oxidative Cyclization of Allylic Sulfamides.
Angew Chem Int Ed Engl. 2010 Jul 26;122(32):5661-5664. doi: 10.1002/ange.200906342.
7
Modular synthesis of 1,2-diamine derivatives by palladium-catalyzed aerobic oxidative cyclization of allylic sulfamides.
Angew Chem Int Ed Engl. 2010 Jul 26;49(32):5529-32. doi: 10.1002/anie.200906342.
本文引用的文献
1
Enantiomeric impurities in chiral synthons, catalysts, and auxiliaries. Part 3.
Tetrahedron Asymmetry. 2006 Oct 27;17(19):2821-2832. doi: 10.1016/j.tetasy.2006.10.014.
2
Sulfinimine-derived 2,3-diamino esters in the asymmetric synthesis of piperidine (2S,3S)-(+)-CP-99,994.
Tetrahedron Lett. 2007 Oct 29;48(44):7838-7840. doi: 10.1016/j.tetlet.2007.08.132.
3
Catalytic asymmetric allylic and homoallylic diamination of terminal olefins via formal C-H activation.
J Am Chem Soc. 2008 Jul 9;130(27):8590-1. doi: 10.1021/ja8027394. Epub 2008 Jun 13.
4
A direct stereoselective approach to trans-2,3-disubstituted piperidines: application in the synthesis of 2-Epi-CP-99,994 and (+)-epilupinine.
Org Lett. 2008 Jun 19;10(12):2473-6. doi: 10.1021/ol800722a. Epub 2008 May 14.
5
Diastereoselective synthesis of delta-aminoacids through domino Ireland-Claisen rearrangement and Michael addition.
Org Lett. 2008 May 1;10(9):1687-90. doi: 10.1021/ol8001464. Epub 2008 Apr 10.
6
Concise asymmetric synthesis of (+)-CP-99,994 and (+)-L-733,060 via efficient construction of homochiral syn-1,2-diamines and syn-1,2-amino alcohols.
J Org Chem. 2008 Apr 18;73(8):3307-10. doi: 10.1021/jo8002979. Epub 2008 Mar 11.
7
Catalytic asymmetric diamination of conjugated dienes and triene.
J Am Chem Soc. 2007 Sep 26;129(38):11688-9. doi: 10.1021/ja074698t. Epub 2007 Sep 6.
8
A facile Pd(0)-catalyzed regio- and stereoselective diamination of conjugated dienes and trienes.
J Am Chem Soc. 2007 Jan 31;129(4):762-3. doi: 10.1021/ja0680562.
9
Bifunctional-thiourea-catalyzed diastereo- and enantioselective aza-Henry reaction.
Chemistry. 2005 Dec 23;12(2):466-76. doi: 10.1002/chem.200500735.
10
Enantio- and diastereoselective catalytic Mannich-type reaction of a glycine schiff base using a chiral two-center phase-transfer catalyst.
Angew Chem Int Ed Engl. 2005 Jul 18;44(29):4564-7. doi: 10.1002/anie.200500927.
Zotero 插件