Comparison of chiral thiazolium and triazolium salts as asymmetric catalysts for the benzoin condensation

被引:199
作者
Knight, RL [1 ]
Leeper, FJ [1 ]
机构
[1] Univ Cambridge, Chem Lab, Cambridge CB2 1EW, England
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1998年 / 12期
关键词
D O I
10.1039/a803635g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Chiral bicyclic 1,2,4-triazolium salts having a defined face of the heterocyclic ring hindered have been synthesised and they catalyse the benzoin condensation in good yield;:the enantiomeric excesses obtained (up to 80%) are much better than with closely related thiazolium salts and the opposite enantiomer of benzoin predominates.
引用
收藏
页码:1891 / 1893
页数:3
相关论文
共 16 条
[2]   Dynamic isomerism involving mobile hydro carbon radicals. Part IV. The rearrangement of 3 : 5-dichloro-substituted triphenylbenzenylamidines. [J].
Chapman, AW ;
Perrott, CH .
JOURNAL OF THE CHEMICAL SOCIETY, 1932, :1770-1775
[3]   NUCLEAR MAGNETIC-RESONANCE ENANTIOMER REAGENTS - CONFIGURATIONAL CORRELATIONS VIA NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF DIASTEREOMERIC MANDELATE, O-METHYLMANDELATE, AND ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETATE (MTPA) ESTERS [J].
DALE, JA ;
MOSHER, HS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) :512-519
[4]   PREPARATION, STRUCTURE, AND REACTIVITY OF 1,3,4-TRIPHENYL-4,5-DIHYDRO-1H-1,2,4-TRIAZOL-5-YLIDENE, A NEW STABLE CARBENE [J].
ENDERS, D ;
BREUER, K ;
RAABE, G ;
RUNSINK, J ;
TELES, JH ;
MELDER, JP ;
EBEL, K ;
BRODE, S .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (09) :1021-1023
[5]   A novel asymmetric benzoin reaction catalyzed by a chiral triazolium salt - Preliminary Communication [J].
Enders, D ;
Breuer, K ;
Teles, JH .
HELVETICA CHIMICA ACTA, 1996, 79 (04) :1217-1221
[6]   Synthesis of and asymmetric induction by chiral polycyclic thiazolium salts [J].
Gerhard, AU ;
Leeper, FJ .
TETRAHEDRON LETTERS, 1997, 38 (20) :3615-3618
[7]   NEW METHODS AND REAGENTS IN ORGANIC-SYNTHESIS .96. STEREOSELECTIVE SYNTHESIS OF 2,3-DIHYDROXY-4-DIMETHYLAMINO-5-METHOXYPENTANOIC ACID, A FRAGMENT OF CALYCULINS - DETERMINATION OF THE ABSOLUTE-CONFIGURATION OF CALYCULINS [J].
HAMADA, Y ;
TANADA, Y ;
YOKOKAWA, F ;
SHIOIRI, T .
TETRAHEDRON LETTERS, 1991, 32 (42) :5983-5986
[8]  
KELLER F, 1966, Patent No. 3265688
[9]   Synthesis of and asymmetric induction by chiral bicyclic thiazolium salts [J].
Knight, RL ;
Leeper, FJ .
TETRAHEDRON LETTERS, 1997, 38 (20) :3611-3614
[10]  
LETTAU H, 1993, PHARMAZIE, V48, P410