Chiral binaphthyl-derived amine-thiourea organocatalyst-promoted asymmetric Morita-Baylis-Hillman reaction

被引：261
作者：
Wang, J
Li, H
Yu, XH
Zu, LS
Wang, W [1 ]
机构：
[1] Univ New Mexico, Dept Chem, Albuquerque, NM 87131 USA
[2] E China Univ Sci & Technol, Coll Pharmaceut Engn, Dept Med Chem, Shanghai 200237, Peoples R China
来源：
ORGANIC LETTERS | 2005年 / 7卷 / 19期
关键词：
D O I：
10.1021/ol051822+
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new bifunctional binaphthyl-derived amine thiourea organocatalyst has been developed to promote enantioselective Morita-Baylis-Hillman reaction of cyclohexenone with a wide range of aldehydes. The process, catalyzed by the amine thiourea, affords synthetically valuable chiral allylic alcohol building blocks in high yields and high enantioselectivities.
引用
收藏
页码：4293 / 4296
页数：4
相关论文
共 49 条
[1]   Metal- and ligand-accelerated catalysis of the Baylis-Hillman reaction [J].
Aggarwal, VK ;
Mereu, A ;
Tarver, GJ ;
McCague, R .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (21) :7183-7189
[2]   A new protocol for the Baylis-Hillman reaction: the reaction of iminium salts prepared in situ with methyl acrylate [J].
Azizi, N ;
Saidi, MR .
TETRAHEDRON LETTERS, 2002, 43 (24) :4305-4308
[3]   Selective formation of α-methylene-β-amino acid derivatives through the aza version of the Baylis-Hillman reaction [J].
Balan, D ;
Adolfsson, H .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (19) :6498-6501
[4]   Asymmetric Baylis-Hillman reactions: catalysis using a chiral pyrrolizidine base [J].
Barrett, AGM ;
Cook, AS ;
Kamimura, A .
CHEMICAL COMMUNICATIONS, 1998, (22) :2533-2534
[5]   Recent advances in the Baylis-Hillman reaction and applications [J].
Basavaiah, D ;
Rao, AJ ;
Satyanarayana, T .
CHEMICAL REVIEWS, 2003, 103 (03) :811-891
[6]   PHOSPHINE MEDIATED SYNTHESIS OF 2-METHYLIDENE-3-AMINO ESTERS AND KETONES [J].
BERTENSHAW, S ;
KAHN, M .
TETRAHEDRON LETTERS, 1989, 30 (21) :2731-2732
[7]  
Breinbauer R, 2000, ANGEW CHEM INT EDIT, V39, P3604, DOI 10.1002/1521-3773(20001016)39:20<3604::AID-ANIE3604>3.0.CO
[8]  
2-9
[9]   HYDROGEN-BOND DIRECTED COCRYSTALLIZATION AND MOLECULAR RECOGNITION PROPERTIES OF DIARYLUREAS [J].
ETTER, MC ;
URBANCZYKLIPKOWSKA, Z ;
ZIAEBRAHIMI, M ;
PANUNTO, TW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (23) :8415-8426
[10]   ENCODING AND DECODING HYDROGEN-BOND PATTERNS OF ORGANIC-COMPOUNDS [J].
ETTER, MC .
ACCOUNTS OF CHEMICAL RESEARCH, 1990, 23 (04) :120-126
12345