Calixarene-based chiral primary amine thiourea promoted highly enantioselective asymmetric Michael reactions of α,α-disubstituted aldehydes with maleimides

被引:31
作者
Durmaz, Mustafa [1 ]
Sirit, Abdulkadir [1 ]
机构
[1] Necmettin Erbakan Univ, Dept Chem, TR-42099 Meram, Konya, Turkey
关键词
CONJUGATE ADDITION; BIFUNCTIONAL ORGANOCATALYSTS; MOLECULAR RECOGNITION; OPTICAL RESOLUTION; SCAFFOLD; CONE; RIM;
D O I
10.1016/j.tetasy.2013.09.010
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Calix[4]arene based chiral bifunctional thiourea-primary amines have been shown to act as effective catalysts for the Michael addition of aldehydes to maleimides for the first time. The corresponding adducts were generally obtained preferentially in (R)- or (S)-forms with high yields (up to 99%) and with high to excellent enantioselectivities (up to 98% ee). (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1443 / 1448
页数:6
相关论文
共 59 条
[31]  
Liu LZ, 2011, CHINESE J ORG CHEM, V31, P964
[32]   Calixarenes for biochemical recognition and separation [J].
Ludwig, R .
MICROCHIMICA ACTA, 2005, 152 (1-2) :1-19
[33]   Tuning and enhancing enantioselective quenching of calixarene hosts by chiral guest Amines [J].
Lynam, C ;
Jennings, K ;
Nolan, K ;
Kane, P ;
McKervey, MA ;
Diamond, D .
ANALYTICAL CHEMISTRY, 2002, 74 (01) :59-66
[34]   Thiourea-catalyzed asymmetric conjugate addition of α-substituted cyanoacetates to maleimides [J].
Ma, Zhi-wei ;
Wu, Ya ;
Sun, Bin ;
Du, Hai-long ;
Shi, Wei-min ;
Tao, Jing-chao .
TETRAHEDRON-ASYMMETRY, 2013, 24 (01) :7-13
[35]   A highly efficient large-scale asymmetric Michael addition of isobutyraldehyde to maleimides promoted by a novel multifunctional thiourea [J].
Ma, Zhi-wei ;
Liu, Yu-xia ;
Li, Pan-li ;
Ren, Hang ;
Zhu, Yu ;
Tao, Jing-chao .
TETRAHEDRON-ASYMMETRY, 2011, 22 (18-19) :1740-1748
[36]   Asymmetric Michael reactions of α,α-disubstituted aldehydes with maleimides using a primary amine thiourea organocatalyst [J].
Miura, Tsuyoshi ;
Masuda, Akira ;
Ina, Mariko ;
Nakashima, Kosuke ;
Nishida, Shohei ;
Tada, Norihiro ;
Itoh, Akichika .
TETRAHEDRON-ASYMMETRY, 2011, 22 (16-17) :1605-1609
[37]   Asymmetric Michael additions of aldehydes to maleimides using a recyclable fluorous thiourea organocatalyst [J].
Miura, Tsuyoshi ;
Nishida, Shohei ;
Masuda, Akira ;
Tada, Norihiro ;
Itoh, Akichika .
TETRAHEDRON LETTERS, 2011, 52 (32) :4158-4160
[38]   Recognition of amino acids by functionalized calixarenes [J].
Mutihac, Lucia ;
Lee, Jae Hong ;
Kim, Jong Seung ;
Vicens, Jacques .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (05) :2777-2796
[39]   Application of L-prolinamides as highly efficient organocatalysts for the asymmetric Michael addition of unmodified aldehydes to nitroalkenes [J].
Naziroglu, Hayriye Nevin ;
Durmaz, Mustafa ;
Bozkurt, Selahattin ;
Demir, Ayhan Sitki ;
Sirit, Abdulkadir .
TETRAHEDRON-ASYMMETRY, 2012, 23 (02) :164-169
[40]   Noncovalent Bifunctional Organocatalysts: Powerful Tools for Contiguous Quaternary-Tertiary Stereogenic Carbon Formation, Scope, and Origin of Enantioselectivity [J].
Nugent, Thomas C. ;
Sadiq, Abdul ;
Bibi, Ahtaram ;
Heine, Thomas ;
Zeonjuk, Lei Liu ;
Vankova, Nina ;
Bassil, Bassem S. .
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (13) :4088-4098