A C-C bond formation reaction at the α-carbon atom of α-oxo ketene dithioacetals via the Baylis-Hillman type reaction

被引：42
作者：
Yin, YB
Wang, M [1 ]
Liu, Q
Hu, JL
Sun, SG
Kang, J
机构：
[1] NE Normal Univ, Dept Chem, Changchun 130024, Peoples R China
[2] Qiqihar Univ, Dept Chem & Chem Engn, Qiqihar 161006, Peoples R China
来源：
TETRAHEDRON LETTERS | 2005年 / 46卷 / 25期
基金：
中国国家自然科学基金;
关键词：
alpha-oxo ketene dithioacetals; activated alkenes; C-C bond; formation; Baylis-Hillman type reaction; double Baylis-Hillman products;
D O I：
10.1016/j.tetlet.2005.04.108
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The first example of TiCl4-mediated Baylis-Hillinan type reaction of alpha-acetyl cyclic ketene dithioacetals with arylaldehydes was described. This methodology adds a new entry to the C-C bond formation at the alpha-carbon atom of alpha-oxo ketene dithioacetals. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码：4399 / 4402
页数：4
相关论文
共 34 条
[11]   Enantiospecific syntheses of pseudopterosin aglycones.: Part 2.: Synthesis of pseudopterosin K-L aglycone and pseudopterosin A-F aglycone via a B→BA→BAC annulation strategy [J].
Kocienski, PJ ;
Pontiroli, A ;
Qun, L .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (19) :2356-2366
[12]   Use of a Baylis-Hillman adduct in the stereoselective synthesis of syributins via a RCM protocol [J].
Krishna, PR ;
Narsingam, M ;
Kannan, V .
TETRAHEDRON LETTERS, 2004, 45 (24) :4773-4775
[13]  
Langer P, 2000, ANGEW CHEM INT EDIT, V39, P3049, DOI 10.1002/1521-3773(20000901)39:17<3049::AID-ANIE3049>3.0.CO
[14]  
2-5
[15]   A new stereospecific synthesis of unusual (Z)-β-branched Baylis-Hillman adducts [J].
Li, GG ;
Wei, HX ;
Willis, S .
TETRAHEDRON LETTERS, 1998, 39 (26) :4607-4610
[16]   TiCl4-Mediated Baylis-Hillman and aldol reactions without the direct use of a Lewis base [J].
Li, GG ;
Wei, HX ;
Gao, JJ ;
Caputo, TD .
TETRAHEDRON LETTERS, 2000, 41 (01) :1-5
[17]   The first nonthiolic, odorless 1,3-propanedithiol equivalent and its application in thioacetalization [J].
Liu, Q ;
Che, GB ;
Yu, HF ;
Liu, YC ;
Zhang, JP ;
Zhang, Q ;
Dong, DW .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (23) :9148-9150
[18]   A novel and facile synthesis of dienals and substituted 2H-pyrans via the Vilsmeier reaction of α-oxo-ketenedithioacetals [J].
Liu, YC ;
Dong, DW ;
Liu, Q ;
Qi, YM ;
Wang, Z .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (01) :28-30
[19]   Electrotelluration: A new approach to tri- and tetrasubstituted alkenes [J].
Marino, JP ;
Nguyen, HN .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (18) :6291-6296
[20]   Baylis-Hillman-type carbon-carbon bond formation of alkenylphosphonates by the action of lithium diisopropylamide [J].
Nagaoka, Y ;
Tomioka, K .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (19) :6428-6429
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