Chiral amino alcohols derived from (S)-6-chloronicotine as catalysts for asymmetric synthesis

被引:12
作者
Capracotta, Sonja S. [1 ]
Comins, Daniel L. [1 ]
机构
[1] N Carolina State Univ, Dept Chem, Raleigh, NC 27695 USA
基金
美国国家科学基金会;
关键词
NICOTINIC ACETYLCHOLINE-RECEPTORS; LIGANDS; SUBSTITUTION; DIETHYLZINC;
D O I
10.1016/j.tetlet.2009.02.012
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Commercially available (S)-nicotine was converted in two or three synthetic steps to various chiral amino alcohols. These nicotine derivatives were evaluated as potential chiral ligands for metal-catalyzed asymmetric reactions by using the addition of diethylzinc to aldehydes as a screen. Several reactions proceeded with a high degree of enantioselectivity providing good yields of secondary alcohols of high enantiopurity. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1806 / 1808
页数:3
相关论文
共 19 条
[1]   Chiral 1,2-amino alcohols and 1,2-diamines derived from cyclohexene oxide: Recent applications in asymmetric synthesis [J].
de Parrodi, Cecilia Anaya ;
Juaristi, Eusebio .
SYNLETT, 2006, (17) :2699-2715
[2]   Regioselective C-2 and C-6 substitution of (S)-nicotine and nicotine derivatives [J].
Février, FC ;
Smith, ED ;
Comins, DL .
ORGANIC LETTERS, 2005, 7 (24) :5457-5460
[3]  
Gros P, 2002, EUR J ORG CHEM, V2002, P3375
[4]   Bifunctional transition metal-based molecular catalysts for asymmetric syntheses [J].
Ikariya, T ;
Murata, K ;
Noyori, R .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (03) :393-406
[5]   Neuronal nicotinic acetylcholine receptors: Structural revelations, target identifications, and therapeutic inspirations [J].
Jensen, AA ;
Frolund, B ;
Lijefors, T ;
Krogsgaard-Larsen, P .
JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (15) :4705-4745
[6]   Emerging structure of the nicotinic acetylcholine receptors [J].
Karlin, A .
NATURE REVIEWS NEUROSCIENCE, 2002, 3 (02) :102-114
[7]   Chiral 8-substituted 10,10-dimethyl-5-pyridin-2-yl-6-aza-tricyclo [7.1.1.02,7]undeca-2(7),3,5-trien-8-ols as enantioselective catalysts in the addition of diethylzinc to substituted benzaldehydes [J].
Lin, RX ;
Chen, CP .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2006, 243 (01) :89-98
[8]  
Lloyd GK, 2000, J PHARMACOL EXP THER, V292, P461
[9]   3,3′-Dipyridyl BINOL ligands.: Synthesis and application in enantioselective addition of Et2Zn to aldehydes [J].
Milburn, Robert R. ;
Hussain, S. M. Shakil ;
Prien, Olaf ;
Ahmed, Zaheer ;
Snieckus, Victor .
ORGANIC LETTERS, 2007, 9 (22) :4403-4406
[10]  
Noyori R., 1994, ASYMMETRIC CATALYSIS