Acid-labile δ-ketal-β-hydroxy esters by asymmetric hydrogenation of corresponding δ-ketal-β-keto esters in the presence of CaCO3

被引:19
作者
Fan, Weizheng [1 ]
Li, Wanfang [1 ]
Ma, Xin [1 ]
Tao, Xiaoming [1 ]
Li, Xiaoming [1 ]
Yao, Ying [1 ]
Xie, Xiaomin [1 ]
Zhang, Zhaoguo [1 ,2 ]
机构
[1] Shanghai Jiao Tong Univ, Sch Chem & Chem Engn, Shanghai 200240, Peoples R China
[2] Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
HIGHLY ENANTIOSELECTIVE HYDROGENATION; RU-BINAP COMPLEX; PRACTICAL SYNTHESIS; LIGANDS; DERIVATIVES; COMPACTIN; SOLVENT; ANALOGS;
D O I
10.1039/c2cc31002c
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A series of acid-labile, optically pure epsilon-substituted delta-ketal-beta-hydroxy esters were obtained by a Ru-SunPhos catalyzed asymmetric hydrogenation of the corresponding epsilon-substituted delta-ketal-beta-keto esters. CaCO3 played a dual role in the hydrogenation reaction-removing the acid generated during the formation of the catalyst and maintaining the activity of the catalyst.
引用
收藏
页码:4247 / 4249
页数:3
相关论文
共 45 条
[1]   New and efficient synthesis of the HMG-CoA reductase inhibitor pitavastatin [J].
Acemoglu, Murat ;
Brodbeck, Andre ;
Garcia, Angel ;
Grimler, Dorninique ;
Hassel, Marc ;
Riss, Bernhard ;
Schreiber, Robert .
HELVETICA CHIMICA ACTA, 2007, 90 (06) :1069-1081
[2]   Highly Stereoselective Hydrogenations-As Key-Steps in the Total Synthesis of Statins [J].
Andrushko, Natalia ;
Andrushko, Vasyl ;
Tararov, Vitali ;
Korostylev, Andrei ;
Koenig, Gerd ;
Boerner, Armin .
CHIRALITY, 2010, 22 (05) :534-541
[3]   Highly enantioselective catalytic hydrogenation of a 5-amino-3,5-dioxopentanoic ester [J].
Andrushko, Vasyl ;
Andrushko, Natalia ;
Koenig, Gerd ;
Boerner, Armin .
TETRAHEDRON LETTERS, 2008, 49 (33) :4836-4839
[4]  
[Anonymous], 2010, CATALYTIC ASYMMETRIC
[5]  
Arbuzov A.E., 1906, J RUSS PHYS CHEM SOC, V38, P687
[6]  
Blandin V, 1999, EUR J ORG CHEM, V1999, P3421
[7]  
Blandin V, 1999, EUR J ORG CHEM, V1999, P1787
[8]   Tuning diastereoselectivity with the solvent: the asymmetric hydrogenation of simple and functionalized 1,3-diketones with ruthenium(amidophosphine-phosphinite) catalysts [J].
Blandin, V ;
Carpentier, JF ;
Mortreux, A .
NEW JOURNAL OF CHEMISTRY, 2000, 24 (05) :309-312
[9]   Historic Overview and Recent Advances in the Synthesis of Super-statins [J].
Casar, Zdenko .
CURRENT ORGANIC CHEMISTRY, 2010, 14 (08) :816-845
[10]  
Cheung KM, 2002, ANGEW CHEM INT EDIT, V41, P1198, DOI 10.1002/1521-3773(20020402)41:7<1198::AID-ANIE1198>3.0.CO