journal article Jan 01, 2016

Copper-catalyzed retro-aldol reaction of β-hydroxy ketones or nitriles with aldehydes: chemo- and stereoselective access to (E)-enones and (E)-acrylonitriles

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Abstract
A mild and efficient copper-catalyzed retro-aldol reaction of β-hydroxy ketones or nitriles with benzaldehydes produces chemo-, regio- and stereoselectively (E)-enones and (E)-acrylonitriles.
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References
64
[1]
Wurtz Bull. Soc. Chim. Fr. (1872)
[2]
Johnson Acc. Chem. Res. (2000) 10.1021/ar960062n
[3]
Denmark Acc. Chem. Res. (2000) 10.1021/ar960027g
[4]
Modern Aldol Reactions, ed. R. Mahrwald, Wiley-VCH, Weinheim, Germany, 2004
[5]
Palomo Chem. Soc. Rev. (2004) 10.1039/b202901d
[6]
Schetter Angew. Chem., Int. Ed. (2006) 10.1002/anie.200602780
[8]
Notz Acc. Chem. Res. (2004) 10.1021/ar0300468
[9]
Mukherjee Chem. Rev. (2007) 10.1021/cr0684016
[10]
Trost Chem. Soc. Rev. (2010) 10.1039/b923537j
[11]
Bisai Tetrahedron (2012) 10.1016/j.tet.2012.03.099
[12]
Zimmerman J. Am. Chem. Soc. (1957) 10.1021/ja01565a041
[13]
Dusselier Top. Curr. Chem. (2014) 10.1007/128_2014_540
[14]
Dusselier Top. Curr. Chem. (2014) 10.1007/128_2014_544
[15]
Reymond Angew. Chem., Int. Ed. Engl. (1995) 10.1002/anie.199522851
[16]
Flanagan J. Am. Chem. Soc. (1996) 10.1021/ja954221u
[18]
List J. Am. Chem. Soc. (1999) 10.1021/ja991507g
[19]
Cordova J. Am. Chem. Soc. (2001) 10.1021/ja001819f
[20]
Schipper Angew. Chem., Int. Ed. (2009) 10.1002/anie.200902373
[21]
Luo Chem. – Eur. J. (2010) 10.1002/chem.201000181
[22]
Flock Chem. – Eur. J. (2010) 10.1002/chem.200903497
[23]
Tosaki J. Am. Chem. Soc. (2006) 10.1021/ja064858l
[24]
Hara Tetrahedron (2009) 10.1016/j.tet.2009.02.031
[25]
Jung Org. Lett. (2012) 10.1021/ol302234a
[26]
Zhang J. Am. Chem. Soc. (2010) 10.1021/ja1035495
[27]
Vashchenko Monatsh. Chem. (2012) 10.1007/s00706-012-0811-8
[28]
Murakami Tetrahedron Lett. (2008) 10.1016/j.tetlet.2008.02.062
[29]
Sodhi Tetrahedron Lett. (2015) 10.1016/j.tetlet.2015.02.057
[30]
Bao Chem. Sci. (2015) 10.1039/c5sc02218e
[31]
Zhang J. Org. Chem. (2016) 10.1021/acs.joc.5b02098
[32]
D. N. Dahr , The Chemistry of Chaleones and Related Compounds, Wiley, New York, 1981
[33]
Guthrie Can. J. Chem. (1984) 10.1139/v84-336
[34]
Sakthivel J. Am. Chem. Soc. (2001) 10.1021/ja010037z
[35]
Wolter Org. Lett. (2002) 10.1021/ol025548k
[36]
Altman J. Org. Chem. (2008) 10.1021/jo702024p
[37]
Niu J. Org. Chem. (2009) 10.1021/jo900600m
[38]
Skraup Monatsh. Chem. (1880) 10.1007/bf01517073
[39]
Ueber eine dem Chinolin homologe Base

O. Doebner, W. v. Miller

Berichte der deutschen chemischen Gesellschaft 1881 10.1002/cber.188101402258
[40]
Friedländer Ber. Dtsch. Chem. Ges. (1882) 10.1002/cber.188201502219
[41]
G. Jones , in Comprehensive Heterocyclic Chemistry, Pergamon Press, New York, 1984, vol. 2, pp. 395–510
[42]
Marco-Contelles Chem. Rev. (2009) 10.1021/cr800482c
[43]
Kouznetsov Tetrahedron (2009) 10.1016/j.tet.2008.12.059
[44]
Bera Eur. J. Inorg. Chem. (2009) 10.1002/ejic.200900312
[45]
Tsuzuki J. Med. Chem. (2004) 10.1021/jm0304966
[46]
Sadhukhan Inorg. Chem. (2009) 10.1021/ic801586d
[47]
Transition metal-catalyzed carbon–carbon bond activation

Chul-Ho Jun

Chemical Society Reviews 2004 10.1039/b308864m
[48]
Recent Advances in Transition-Metal-Catalyzed Functionalization of Unstrained Carbon–Carbon Bonds

Feng Chen, Teng Wang, Ning Jiao

Chemical Reviews 2014 10.1021/cr400628s
[49]
C–C bond activation, in Topics in Current Chemistry, ed. G. Dong, Springer-Verlag, Berlin, 2014, vol. 346
[50]
Catalytic C–C Bond Activations via Oxidative Addition to Transition Metals

Laetitia Souillart, Nicolai Cramer

Chemical Reviews 2015 10.1021/acs.chemrev.5b00138

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Details
Published
Jan 01, 2016
Vol/Issue
14(30)
Pages
7282-7294
Funding
National Natural Science Foundation of China Award: 21472068,21202062
National Natural Science Foundation of Jiangsu Province Award: BK2012108
Cite This Article
Song-Lin Zhang, Zhu-Qin Deng (2016). Copper-catalyzed retro-aldol reaction of β-hydroxy ketones or nitriles with aldehydes: chemo- and stereoselective access to (E)-enones and (E)-acrylonitriles. Organic & Biomolecular Chemistry, 14(30), 7282-7294. https://doi.org/10.1039/c6ob01198e
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