Camphoric acid derived sulfur containing bicyclic carboxylic acids as chiral auxiliaries in N-acyliminium ion chemistry

被引:4
作者
Braeckow, J. [2 ]
Pabel, J. [1 ]
Mayer, R. [3 ]
Polborn, K. [3 ]
Wanner, K. T. [1 ]
机构
[1] Univ Munich, Dept Pharm, Zentrum Pharmaforsch, D-81377 Munich, Germany
[2] Carbogen Amcis AG, CH-5502 Hunzenschwil, Switzerland
[3] Univ Munich, Dept Chem, D-81377 Munich, Germany
关键词
N-Acyliminium salt; Asymmetric synthesis; Asymmetric electrophilic alpha-amidoalkylation (AE alpha A); Thioanhydride; Thiolactone; ELECTROPHILIC ALPHA-AMIDOALKYLATION; ASYMMETRIC-SYNTHESIS; ACYLPYRIDINIUM IONS; ADDITION-REACTIONS; GENERATION; QUINOLINES; CHLORIDE;
D O I
10.1016/j.tet.2010.07.009
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Three novel sulfur containing chiral bicyclic carboxylic acids were synthesized from D-camphoric acid. Two of these compounds were briefly evaluated for their potency as chiral auxiliaries in Asymmetric Electrophilic alpha-Amidoalkylation (AE alpha A) reactions. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码:7279 / 7287
页数:9
相关论文
共 20 条
[1]  
HOEFNER G, 2000, Patent No. [00140645, 000140645]
[2]   Generation of chiral N-acylpyridinium ions by means of silyl triflates and their diastereoselective trapping reactions:: formation of N-acyldihydropyridines and N-acyldihydropyridones [J].
Hoesl, CE ;
Maurus, M ;
Pabel, J ;
Polborn, K ;
Wanner, KT .
TETRAHEDRON, 2002, 58 (33) :6757-6770
[3]   PREPARATION OF (-)-(1S,4R)-CAMPHANOYL CHLORIDE [2-OXABICYCLO[2.2.1]HEPTANE-1-CARBONYL CHLORIDE, 4,7,7-TRIMETHYL-3-OXO, (1S)-] [J].
KAPPES, D ;
GERLACH, H .
SYNTHETIC COMMUNICATIONS, 1990, 20 (04) :581-587
[4]   Recent developments in the chemistry of dihydropyridines [J].
Lavilla, R .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (09) :1141-1156
[5]   Synthesis of enantiomerically pure sulfenimines and sulfinimines derived from (+)-camphor [J].
Li, Y ;
Zhu, W ;
Cheng, ZY ;
Yang, GS .
SYNTHETIC COMMUNICATIONS, 1999, 29 (15) :2645-2656
[6]  
Ludwig M, 2003, HETEROCYCLES, V61, P299
[7]  
Müller P, 2001, HELV CHIM ACTA, V84, P1093
[8]   Generation of N-acylpyridinium ions from pivaloyl chloride and pyridine derivatives by means of silyl triflates [J].
Pabel, J ;
Hösl, CE ;
Maurus, M ;
Ege, M ;
Wanner, KT .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (26) :9272-9275
[9]  
Perrin D.D., 1988, PURIFICATION LAB CHE, V3
[10]  
Pilli R. A., 2004, SCI SYNTHESIS, V27, P375