双乙酸酯酮催化的烯烃不对称环氧化反应。
A diacetate ketone-catalyzed asymmetric epoxidation of olefins.
作者信息
Wang Bin, Wu Xin-Yan, Wong O Andrea, Nettles Brian, Zhao Mei-Xin, Chen Dajun, 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 May 15;74(10):3986-9. doi: 10.1021/jo900330n.
Abstract
A fructose-derived diacetate ketone has been shown to be an effective catalyst for asymmetric epoxidation. High ee values have been obtained for a variety of trans and trisubstituted olefins including electron-deficient alpha,beta-unsaturated esters as well as certain cis olefins.
摘要
一种果糖衍生的二乙酸酮已被证明是一种有效的不对称环氧化催化剂。对于各种反式和三取代烯烃，包括缺电子的α,β-不饱和酯以及某些顺式烯烃，都获得了高对映体过量（ee）值。
相似文献
1
A diacetate ketone-catalyzed asymmetric epoxidation of olefins.
J Org Chem. 2009 May 15;74(10):3986-9. doi: 10.1021/jo900330n.
2
Practical synthesis of an L-fructose-derived ketone catalyst for asymmetric epoxidation of olefins.
J Org Chem. 2006 Jul 7;71(14):5377-9. doi: 10.1021/jo060335k.
3
Asymmetric epoxidation catalyzed by alpha,alpha-dimethylmorpholinone ketone. Methyl group effect on spiro and planar transition states.
J Org Chem. 2009 Aug 21;74(16):6335-8. doi: 10.1021/jo900739q.
4
Designing new chiral ketone catalysts. Asymmetric epoxidation of cis-olefins and terminal olefins.
J Org Chem. 2002 Apr 19;67(8):2435-46. doi: 10.1021/jo010838k.
5
An improved synthesis of a ketone catalyst for asymmetric epoxidation of olefins.
J Org Chem. 2003 Jun 13;68(12):4963-5. doi: 10.1021/jo0206770.
6
Highly enantioselective epoxidation of alpha, beta-unsaturated esters by chiral dioxirane.
J Am Chem Soc. 2002 Jul 31;124(30):8792-3. doi: 10.1021/ja020478y.
7
Chiral ketone and iminium catalysts for olefin epoxidation.
Top Curr Chem. 2010;291:201-32. doi: 10.1007/978-3-642-02815-1_16.
8
Enantioselective epoxidation of electron-deficient olefins: an organocatalytic approach.
Chem Rec. 2011 Feb;11(1):18-39. doi: 10.1002/tcr.201000006. Epub 2010 Nov 30.
9
Asymmetric Epoxidation of Olefins with Sodium Percarbonate Catalyzed by -amino--pyridine Manganese Complexes.
Molecules. 2022 Apr 14;27(8):2538. doi: 10.3390/molecules27082538.
10
Arabinose-derived ketones as catalysts for asymmetric epoxidation of alkenes.
J Org Chem. 2005 Sep 2;70(18):7279-89. doi: 10.1021/jo050928f.
引用本文的文献
1
Engineering 2-Deoxy-D-ribose-5-phosphate Aldolase for anti- and syn-Selective Epoxidations of α,β-Unsaturated Aldehydes.
Angew Chem Int Ed Engl. 2025 May 12;64(20):e202503054. doi: 10.1002/anie.202503054. Epub 2025 Mar 7.
2
Studies on asymmetric total synthesis of (-)-β-hydrastine a chiral epoxide ring-opening cascade cyclization strategy.
RSC Adv. 2020 May 19;10(32):18953-18958. doi: 10.1039/d0ra03038d. eCollection 2020 May 14.
3
Synthesis and Applications of Carbohydrate-Based Organocatalysts.
Molecules. 2021 Nov 30;26(23):7291. doi: 10.3390/molecules26237291.
4
Total Synthesis of the Marine Ladder Polyether Gymnocin B.
J Am Chem Soc. 2019 Jul 17;141(28):11239-11244. doi: 10.1021/jacs.9b04696. Epub 2019 Jul 8.
5
Function-Oriented Investigations of a Peptide-Based Catalyst that Mediates Enantioselective Allylic Alcohol Epoxidation.
Chem Sci. 2014 Nov 1;5(11):4504-4511. doi: 10.1039/C4SC01440E.
6
Asymmetric synthesis of anti-β-amino-α-hydroxy esters via dynamic kinetic resolution of β-amino-α-keto esters.
Org Lett. 2013 May 17;15(10):2446-9. doi: 10.1021/ol4009206. Epub 2013 Apr 30.
7
Iron-catalyzed asymmetric epoxidation of β,β-disubstituted enones.
J Am Chem Soc. 2011 Jun 8;133(22):8432-5. doi: 10.1021/ja201873d. Epub 2011 May 16.
8
Total synthesis of the protein phosphatase 2A inhibitor lactodehydrothyrsiferol.
Angew Chem Int Ed Engl. 2011 May 23;50(22):5178-81. doi: 10.1002/anie.201007757. Epub 2011 Apr 21.
9
Scalable and efficient synthesis of the mycolactone core.
Tetrahedron. 2010 Mar 27;66(13):2263-2272. doi: 10.1016/j.tet.2010.02.010.
10
Asymmetric epoxidation of fluoroolefins by chiral dioxirane. Fluorine effect on enantioselectivity.
J Org Chem. 2009 Nov 6;74(21):8377-80. doi: 10.1021/jo901553t.
本文引用的文献
1
Organocatalytic oxidation. Asymmetric epoxidation of olefins catalyzed by chiral ketones and iminium salts.
Chem Rev. 2008 Sep;108(9):3958-87. doi: 10.1021/cr068367v. Epub 2008 Jul 1.
2
Enantioselective epoxidation of conjugated cis-enynes by chiral dioxirane.
J Org Chem. 2007 May 25;72(11):4093-7. doi: 10.1021/jo070205r. Epub 2007 Apr 26.
3
Enantioselective synthesis of gamma-aryl-gamma-butyrolactones by sequential asymmetric epoxidation, ring expansion, and Baeyer-Villiger oxidation.
J Org Chem. 2006 Dec 8;71(25):9519-21. doi: 10.1021/jo061341j.
4
Regio- and enantioselective epoxidation of dienes by a chiral dioxirane: synthesis of optically active vinyl cis-epoxides.
Angew Chem Int Ed Engl. 2006 Jul 3;45(27):4475-8. doi: 10.1002/anie.200600840.
5
Studies of substituent effect on asymmetric epoxidation of chromenes by chiral dioxirane.
J Org Chem. 2006 May 12;71(10):3973-6. doi: 10.1021/jo0604179.
6
Effective asymmetric epoxidation of styrenes by chiral dioxirane.
J Org Chem. 2006 Feb 17;71(4):1715-7. doi: 10.1021/jo0520285.
7
Enantioselective synthesis of 2-aryl cyclopentanones by asymmetric epoxidation and epoxide rearrangement.
Angew Chem Int Ed Engl. 2006 Feb 20;45(9):1429-32. doi: 10.1002/anie.200501520.
8
Practical synthesis of Shi's diester fructose derivative for catalytic asymmetric epoxidation of alkenes.
J Org Chem. 2005 Nov 25;70(24):10143-6. doi: 10.1021/jo051682h.
9
Oligopeptides as catalysts for asymmetric epoxidation.
Biopolymers. 2006;84(1):74-89. doi: 10.1002/bip.20373.
10
Ketone-catalyzed asymmetric epoxidation reactions.
Acc Chem Res. 2004 Aug;37(8):497-505. doi: 10.1021/ar030065h.
Zotero 插件