源自(S)-二苯基脯氨醇的新型二甲氧基(氨基烷氧基)硼酸盐作为前手性酮对映选择性硼介导还原反应的高效催化剂。
Novel dimethoxy(aminoalkoxy)borate derived from (S)-diphenylprolinol as highly efficient catalyst for the enantioselective boron-mediated reduction of prochiral ketones.
作者信息
Stepanenko Viatcheslav, Ortiz-Marciales Margarita, Barnes Charles L, Garcia Carmelo
机构信息
Department of Chemistry, University of Puerto Rico - Humacao, CUH Station, Humacao, Puerto Rico 00791, USA.
出版信息
Tetrahedron Lett. 2009 Mar 4;50(9):995-998. doi: 10.1016/j.tetlet.2008.12.061.
Abstract
The novel dimethoxyl(aminoalkoxy)borate 1 was isolated as a white crystalline dimer joined by H-bonding as evidenced by X-ray analysis, and demonstrated to be a highly effective catalyst for the asymmetric reduction of representative prochiral ketones with borane-DMS. Optically pure alcohols were obtained using only 1 mol% of catalyst 1 in up to 99% ee.
摘要
新型二甲氧基（氨基烷氧基）硼酸盐1经分离得到白色结晶二聚体，通过X射线分析证明其通过氢键连接，并被证明是用硼烷-二甲硫醚对代表性前手性酮进行不对称还原的高效催化剂。仅使用1 mol%的催化剂1，即可获得高达99%对映体过量的光学纯醇。
相似文献
1
Novel dimethoxy(aminoalkoxy)borate derived from (S)-diphenylprolinol as highly efficient catalyst for the enantioselective boron-mediated reduction of prochiral ketones.
Tetrahedron Lett. 2009 Mar 4;50(9):995-998. doi: 10.1016/j.tetlet.2008.12.061.
2
Preparation of highly optically pure homochiral sulfide-containing alcohols via oxazaborolidine-catalyzed asymmetric borane reduction of ketones.
Chirality. 2004 Jul;16(6):341-6. doi: 10.1002/chir.20048.
3
Enantioselective Reduction of Prochiral Ketones using Spiroborate Esters as Catalysts.
Tetrahedron Lett. 2007 Aug 13;48(33):5799-5802. doi: 10.1016/j.tetlet.2007.06.086.
4
Chiral spiroaminoborate ester as a highly enantioselective and efficient catalyst for the borane reduction of furyl, thiophene, chroman and thiochroman containing ketones.
Tetrahedron Asymmetry. 2009 Dec 11;20(23):2659-2665. doi: 10.1016/j.tetasy.2009.11.009.
5
β-Hydroxyamide-based ligands and their use in the enantioselective borane reduction of prochiral ketones.
Chirality. 2014 Jan;26(1):21-6. doi: 10.1002/chir.22254. Epub 2013 Nov 6.
6
Effect of temperature on the enantioselectivity in the oxazaborolidine-catalyzed asymmetric reduction of ketones. Noncatalytic borane reduction, a nonneglectable factor in the reduction system.
J Org Chem. 2003 Dec 26;68(26):10146-51. doi: 10.1021/jo035203v.
7
Enantioselective reduction of prochiral ketones by catecholborane catalysed by chiral group 13 complexes.
Chemistry. 2000 Oct 2;6(19):3586-94. doi: 10.1002/1521-3765(20001002)6:19<3586::aid-chem3586>3.0.co;2-s.
8
Facile Stereoselective Reduction of Prochiral Ketones by using an F -dependent Alcohol Dehydrogenase.
Chembiochem. 2021 Jan 5;22(1):156-159. doi: 10.1002/cbic.202000651. Epub 2020 Oct 23.
9
Synthesis of a new C(2)-symmetric chiral catalyst and its application in the catalytic asymmetric borane reduction of prochiral ketones.
Chirality. 2008 Feb;20(2):110-4. doi: 10.1002/chir.20503.
10
Asymmetric Borane Reduction of Prochiral Ketones Catalyzed By Helical Poly[(S)-3-vinyl-2,2'-dihydroxy-1,1'-binaphthyl].
Chirality. 2015 Jul;27(7):422-4. doi: 10.1002/chir.22459. Epub 2015 May 15.
引用本文的文献
1
Synthesis of enantiopure 1,2-azido and 1,2-amino alcohols regio- and stereoselective ring-opening of enantiopure epoxides by sodium azide in hot water.
Tetrahedron Asymmetry. 2016 Feb 15;27(2-3):91-100. doi: 10.1016/j.tetasy.2015.12.002.
2
Synthesis and stability of new spiroaminoborate esters.
Tetrahedron Lett. 2012 Feb 22;53(8):910-913. doi: 10.1016/j.tetlet.2011.12.054.
3
Chiral epoxides via borane reduction of 2-haloketones catalyzed by spiroborate ester: application to the synthesis of optically pure 1,2-hydroxy ethers and 1,2-azido alcohols.
J Org Chem. 2011 Mar 18;76(6):1883-6. doi: 10.1021/jo102294j. Epub 2011 Feb 4.
4
5
Chiral spiroaminoborate ester as a highly enantioselective and efficient catalyst for the borane reduction of furyl, thiophene, chroman and thiochroman containing ketones.
Tetrahedron Asymmetry. 2009 Dec 11;20(23):2659-2665. doi: 10.1016/j.tetasy.2009.11.009.
6
Spiroborate ester-mediated asymmetric synthesis of beta-hydroxy ethers and its conversion to highly enantiopure beta-amino ethers.
J Org Chem. 2009 Jun 5;74(11):4195-202. doi: 10.1021/jo900666r.
7
Highly enantioselective borane reduction of heteroaryl and heterocyclic ketoxime ethers catalyzed by novel spiroborate ester derived from diphenylvalinol: application to the synthesis of nicotine analogues.
J Org Chem. 2008 Jun 6;73(11):4017-26. doi: 10.1021/jo800204n. Epub 2008 May 1.
本文引用的文献
1
Reduction of Carbonyl Compounds with Chiral Oxazaborolidine Catalysts: A New Paradigm for Enantioselective Catalysis and a Powerful New Synthetic Method.
Angew Chem Int Ed Engl. 1998 Aug 17;37(15):1986-2012. doi: 10.1002/(SICI)1521-3773(19980817)37:15<1986::AID-ANIE1986>3.0.CO;2-Z.
2
Spiroborate esters in the borane-mediated asymmetric synthesis of pyridyl and related heterocyclic alcohols.
Tetrahedron Asymmetry. 2007 Nov 26;18(23):2738-2745. doi: 10.1016/j.tetasy.2007.10.044.
3
Enantioselective Reduction of Prochiral Ketones using Spiroborate Esters as Catalysts.
Tetrahedron Lett. 2007 Aug 13;48(33):5799-5802. doi: 10.1016/j.tetlet.2007.06.086.
4
Enantioselective beta-lactone formation from ketene and aldehydes catalyzed by a chiral oxazaborolidine.
Org Lett. 2006 Oct 12;8(21):4943-5. doi: 10.1021/ol061979h.
5
Influences of electronic effects and anions on the enantioselectivity in the oxazaborolidine-catalyzed asymmetric borane reduction of ketones.
J Org Chem. 2004 Oct 1;69(20):6860-6. doi: 10.1021/jo048959i.
6
Effect of temperature on the enantioselectivity in the oxazaborolidine-catalyzed asymmetric reduction of ketones. Noncatalytic borane reduction, a nonneglectable factor in the reduction system.
J Org Chem. 2003 Dec 26;68(26):10146-51. doi: 10.1021/jo035203v.
Zotero 插件