Enantioselective 1,4-addition of kojic acid derivatives to β-nitroolefins catalyzed by a cinchonine derived sugar thiourea

被引:21
作者
Reddy, B. V. Subba [1 ]
Reddy, S. Madhusudana [1 ]
Swain, Manisha [1 ]
Dudem, Srikanth [2 ]
Kalivendi, Shasi V. [2 ]
Reddy, C. Suresh [3 ]
机构
[1] Indian Inst Chem Technol, Hyderabad 500607, Andhra Pradesh, India
[2] Indian Inst Chem Technol, Ctr Chem Biol, Hyderabad 500607, Andhra Pradesh, India
[3] Sri Venkateswra Univ, Dept Chem, Tirupati, Andhra Pradesh, India
关键词
MICHAEL ADDITION; CONJUGATE ADDITION; TUMOR PROMOTERS; CHALCONES; DESIGN; AMIDE;
D O I
10.1039/c3ra47423b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A highly enantioselective Michael addition reaction of kojic acid derivatives to beta-nitroolefins has been accomplished using a cinchonine derived sugar thiourea. The reaction provides the corresponding Michael adducts in excellent yields with a high degree of enantioselectivity (up to 99% ee) in short reaction time with low catalyst loading. The Michael adducts are found to exhibit promising cytotoxicity against various cancer cell lines.
引用
收藏
页码:9107 / 9111
页数:5
相关论文
共 47 条
[31]   Kojyl thioether derivatives having both tyrosinase inhibitory and anti-inflammatory properties [J].
Rho, Ho Sik ;
Ahn, Soo Mi ;
Yoo, Dae Sung ;
Kim, Myung Kyoo ;
Cho, Dong Ha ;
Cho, Jae Youl .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (22) :6569-6571
[32]   β-Peptidic Peptidomimetics [J].
Seebach, Dieter ;
Gardiner, James .
ACCOUNTS OF CHEMICAL RESEARCH, 2008, 41 (10) :1366-1375
[33]   Enantioselective Preparation of β2-Amino Acid Derivatives for β-Peptide Synthesis [J].
Seebach, Dieter ;
Beck, Albert K. ;
Capone, Stefania ;
Deniau, Gildas ;
Groselj, Uros ;
Zass, Engelbert .
SYNTHESIS-STUTTGART, 2009, (01) :1-32
[34]   SYNTHESIS OF FUSED PYRIMIDONE DERIVATIVES OF 4-PYRONES FROM THE ACETATES OF BAYLIS-HILLMAN ADDUCTS [J].
Shahrisa, A. ;
Ghasemi, Z. .
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2010, 46 (01) :30-36
[35]   One-step synthesis of substituted 4,8-dihydropyrano[3,2-b]pyran-4-ones [J].
Shestopalov, AA ;
Rodinovskaya, LA ;
Shestopalov, AM ;
Litvinov, VP .
RUSSIAN CHEMICAL BULLETIN, 2004, 53 (03) :724-725
[36]   Highly enantioselective conjugate addition of nitromethane to chalcones using bifunctional cinchona organocatalysts [J].
Vakulya, B ;
Varga, S ;
Csámpai, A ;
Soós, T .
ORGANIC LETTERS, 2005, 7 (10) :1967-1969
[37]   Epi-cinchona based thiourea organocatalyst family as an efficient asymmetric Michael addition promoter:: Enantioselective conjugate addition of nitroalkanes to chalcones and α,β-unsaturated N-acylpyrroles [J].
Vakulya, Benedek ;
Varga, Szilard ;
Soos, Tibor .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (09) :3475-3480
[38]   Organocatalytic enantioselective Michael addition of a kojic acid derivative to nitro olefins [J].
Wang, Jiyu ;
Zhang, Qing ;
Zhang, Hui ;
Feng, Yujun ;
Yuan, Weicheng ;
Zhang, Xiaomei .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (15) :2950-2954
[39]   PREPARATION AND CYCLOADDITIONS OF A 4-METHOXY-3-OXIDOPYRYLIUM YLIDE - A REAGENT FOR THE SYNTHESIS OF HIGHLY SUBSTITUTED 7-MEMBERED RINGS AND TETRAHYDROFURANS [J].
WENDER, PA ;
MASCARENAS, JL .
TETRAHEDRON LETTERS, 1992, 33 (16) :2115-2118
[40]   STUDIES ON TUMOR PROMOTERS .11. A NEW [5+2] CYCLOADDITION METHOD AND ITS APPLICATION TO THE SYNTHESIS OF BC RING PRECURSORS OF PHOBOIDS [J].
WENDER, PA ;
MASCARENAS, JL .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (22) :6267-6269