Synthesis of cyclopentenyl and cyclohexenyl ketones via [3+2] and [4+2] annulations of 1,2-allenic ketones

被引:8
作者
Cui, Liang-Yan [1 ]
Guo, Sheng-Hai [1 ]
Li, Bin [1 ]
Zhang, Xin-Ying [1 ]
Fan, Xue-Sen [1 ]
机构
[1] Henan Normal Univ, Sch Chem & Chem Engn, Key Lab Green Chem Media & React, Minist Educ,Henan Key Lab Environm Pollut Control, Xinxiang 453007, Peoples R China
基金
中国国家自然科学基金;
关键词
Cyclopentenyl ketone; Cyclohexenyl ketone; 1,2-Allenic ketone; Phosphine-catalyzed annulation; PHOSPHINE CATALYSIS; EFFICIENT; CYCLOADDITION; ALLENOATES; ALDEHYDES; ALLENES;
D O I
10.1016/j.cclet.2013.10.008
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In this paper, an efficient synthesis of cyclopentenyl ketones and cyclohexenyl ketones through tertiary phosphine catalyzed [3 + 2] and [4 + 2] annulations of 1,2-allenic ketones with activated alkenes has been developed. Compared with published synthetic methods on cyclopentenyl ketones and cyclohexenyl ketones, the protocols developed in this paper have the advantages such as readily available starting materials, mild reaction conditions and high efficiency. (C) 2013 Xue-Sen Fan. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
引用
收藏
页码:55 / 57
页数:3
相关论文
共 32 条
[1]   Highly anti-selective SN2′ substitutions of chiral cyclic 2-iodo-allylic alcohol derivatives with mixed zinc-copper reagents [J].
Calaza, MI ;
Hupe, E ;
Knochel, P .
ORGANIC LETTERS, 2003, 5 (07) :1059-1061
[2]   A torquoselective extrusion of isoxazoline N-oxides. Application to the synthesis of aryl vinyl and divinyl ketones for Nazarov cyclization [J].
Canterbury, Daniel P. ;
Herrick, Ildiko R. ;
Um, Joann ;
Houk, K. N. ;
Frontier, Alison J. .
TETRAHEDRON, 2009, 65 (16) :3165-3179
[3]   Phosphane-Catalyzed [4+2] Annulation of Allenoates with Ketimines: Synthesis of Sultam-Fused Tetrahydropyridines [J].
Chen, Xiang-Yu ;
Ye, Song .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (29) :5723-5728
[4]   β-iodoallenolates as Springboards for Annulation Reactions [J].
Ciesielski, Jennifer ;
Canterbury, Daniel P. ;
Frontier, Alison J. .
ORGANIC LETTERS, 2009, 11 (19) :4374-4377
[5]   Alcohol-assisted phosphine catalysis: One-step syntheses of dihydropyrones from aldehydes and allenoates [J].
Creech, Gardner S. ;
Kwon, Ohyun .
ORGANIC LETTERS, 2008, 10 (03) :429-432
[6]   A facile synthetic route to 2H-chromenes:: Reconsideration of the mechanism of the DBU-catalyzed reaction between salicylic aldehydes and ethyl 2-methylbuta-2,3-dienoate [J].
Dai, Lun-Zhi ;
Shi, Yong-Ling ;
Zhao, Gui-Ling ;
Shi, Min .
CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (13) :3701-3706
[7]   Efficient cu-catalyzed asymmetric conjugate additions of alkylzincs to trisubstituted cyclic enones [J].
Degrado, SJ ;
Mizutani, H ;
Hoveyda, AH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (45) :13362-13363
[8]   A phosphine-catalyzed [3+2] cycloaddition strategy leading to the first total synthesis of (-)-hinesol [J].
Du, YS ;
Lu, XY .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (16) :6463-6465
[9]   Highly regioselective construction of spirocycles via phosphine-catalyzed [3+2]-cycloaddition [J].
Du, YS ;
Lu, XY ;
Yu, YH .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (25) :8901-8905
[10]   Tandem Reactions Leading to Bicyclic Pyrimidine Nucleosides and Benzopyran-4-ones [J].
Fan, Xuesen ;
Wang, Yangyang ;
Qu, Yingying ;
Xu, Haiyun ;
He, Yan ;
Zhang, Xinying ;
Wang, Jianji .
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (03) :982-985