A practical synthesis of (S)-2-Cyclohexyl-2-phenylglycolic acid via organocatalytic asymmetric construction of a tetrasubstituted carbon center

被引:112
作者
Tokuda, O [1 ]
Kano, T
Gao, WG
Ikemoto, T
Maruoka, K
机构
[1] Kyoto Univ, Grad Sch Sci, Dept Chem, Sakyo Ku, Kyoto 6068502, Japan
[2] Sumitomo Chem Co Ltd, Fine Chem Res Lab, Nishiyodogawa Ku, Osaka 5550021, Japan
关键词
D O I
10.1021/ol052164w
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A concise and enantioselective synthesis of (S)-2-cyclohexyl-2-phenylglycolic acid as a key intermediate for (S)-oxybutynin is reported. The crucial asymmetric tetrasubstituted carbon center was constructed with excellent stereoselectivity through the proline-catalyzed direct asymmetric aldol reaction between cyclohexanone and ethyl phenylglyoxylate under mild conditions.
引用
收藏
页码:5103 / 5105
页数:3
相关论文
共 24 条
[1]  
BAKALE RP, Patent No. 6140529
[2]  
Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P130
[3]   Direct catalytic asymmetric aldol reactions of aldehydes [J].
Bogevig, A ;
Kumaragurubaran, N ;
Jorgensen, KA .
CHEMICAL COMMUNICATIONS, 2002, (06) :620-621
[4]   In the golden age of organocatalysis [J].
Dalko, PI ;
Moisan, L .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (39) :5138-5175
[5]   TOTAL SYNTHESIS OF OPTICALLY ACTIVE STEROIDS .6. NEW TYPE OF ASYMMETRIC CYCLIZATION TO OPTICALLY ACTIVE STEROID CD PARTIAL STRUCTURES [J].
EDER, U ;
SAUER, G ;
WEICHERT, R .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1971, 10 (07) :496-&
[6]   Chiral mandelic acid template provides a highly practical solution for (S)-oxybutynin synthesis [J].
Grover, PT ;
Bhongle, NN ;
Wald, SA ;
Senanayake, CH .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (19) :6283-6287
[7]   An asymmetric dihydroxylation route to (S)-oxybutynin [J].
Gupta, P ;
Fernandes, RA ;
Kumar, P .
TETRAHEDRON LETTERS, 2003, 44 (22) :4231-4232
[8]   ASYMMETRIC SYNTHESIS OF BICYCLIC INTERMEDIATES OF NATURAL PRODUCT CHEMISTRY [J].
HAJOS, ZG ;
PARRISH, DR .
JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (12) :1615-1621
[9]   Proline-catalyzed asymmetric reactions [J].
List, B .
TETRAHEDRON, 2002, 58 (28) :5573-5590
[10]   Proline-catalyzed direct asymmetric aldol reactions [J].
List, B ;
Lerner, RA ;
Barbas, CF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (10) :2395-2396