Synthesis of Binaphthyl Sulfonimides and Their Application in the Enantioselective Michael Addition of Ketones to Nitroalkenes

被引:39
作者
Ban, Shurong [1 ,2 ]
Du, Da-Ming [1 ]
Liu, Han [3 ]
Yang, Wen [1 ]
机构
[1] Beijing Inst Technol, Sch Chem Engn & Environm, Beijing 100081, Peoples R China
[2] Shanxi Med Univ, Sch Pharmaceut Sci, Taiyuan 030001, Peoples R China
[3] Peking Univ, BNLMS, Coll Chem & Mol Engn, Beijing 100871, Peoples R China
基金
中国国家自然科学基金;
关键词
Sulfonamides; Organocatalysis; Enantioselectivity; Michael addition; Alkenes; TRANSFER HYDROGENATION ATH; ALDOL REACTIONS; PYRROLIDINE SULFONAMIDE; CONJUGATE ADDITION; DIETHYLZINC ADDITION; ASYMMETRIC ADDITION; TI(IV) COMPLEX; ALDEHYDES; ORGANOCATALYSTS; LIGANDS;
D O I
10.1002/ejoc.201000818
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Novel types of L-proline-based binaphthyl sulfonimides and sulfonamides were found to be efficient organocatalysts for the asymmetric Michael addition of ketones to nitroalkenes to provide optically active gamma-nitroketone derivatives of synthetic and biological importance. After the fine optimization of solvents, temperature, and additive, good to excellent enantioselectivities and diastereoselectivities (71-96 % ee, up to >99:1 dr) can be achieved.
引用
收藏
页码:5160 / 5164
页数:5
相关论文
共 57 条
[31]   (S)-Pyrrolidine sulfonamide catalyzed asymmetric direct aldol reactions of aryl methyl ketones with aryl aldehydes [J].
Mei, Kui ;
Zhang, Shilel ;
He, Songtao ;
Li, Ping ;
Jin, Mel ;
Xue, Fei ;
Luo, Guangshun ;
Zhang, Haoyi ;
Song, Lirong ;
Duan, Wenhu ;
Wang, Wei .
TETRAHEDRON LETTERS, 2008, 49 (17) :2681-2684
[32]   Direct asymmetric aldol reactions in brine using novel sulfonamide catalyst [J].
Miura, Tsuyoshi ;
Yasaku, Yumi ;
Koyata, Naka ;
Murakami, Yasuoki ;
Imai, Nobuyuki .
TETRAHEDRON LETTERS, 2009, 50 (22) :2632-2635
[33]   Asymmetric enamine catalysis [J].
Mukherjee, Santanu ;
Yang, Jung Woon ;
Hoffmann, Sebastian ;
List, Benjamin .
CHEMICAL REVIEWS, 2007, 107 (12) :5471-5569
[34]   1,4-addition of diethylzinc to cyclohexenone catalyzed by CuOTf-sulfonamide combined system. Evidence supporting a concerted mechanism [J].
Nakano, K ;
Bessho, Y ;
Kitamura, M .
CHEMISTRY LETTERS, 2003, 32 (03) :224-225
[35]   Ionic Liquid-Supported (ILS) (S)-Pyrrolidine Sulfonamide, a Recyclable Organocatalyst for the Highly Enantioselective Michael Addition to Nitroolefins [J].
Ni, Bukuo ;
Zhang, Qianying ;
Dhungana, Kritanjali ;
Headley, Allan D. .
ORGANIC LETTERS, 2009, 11 (04) :1037-1040
[36]   Synthesis and crystal structures of bis(sulfonamido) titanium bis(alkoxide) complexes: Mechanistic implications in the bis(sulfonamide) catalyzed asymmetric addition of dialkylzinc reagents to aldehydes [J].
Pritchett, S ;
Woodmansee, DH ;
Gantzel, P ;
Walsh, PJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (25) :6423-6424
[37]   Highly Enantioselective Addition of Terminal Alkynes to Aldehydes Catalyzed by a New Chiral β-Sulfonamide Alcohol/Ti(OiPr)4/Et2Zn/R3N Catalyst System [J].
Qiu, Li ;
Wang, Quan ;
Lin, Li ;
Liu, Xiaodong ;
Jiang, Xianxing ;
Zhao, Qingyang ;
Hu, Guowen ;
Wang, Rui .
CHIRALITY, 2009, 21 (02) :316-323
[38]   Amino acid catalyzed direct asymmetric aldol reactions: A bioorganic approach to catalytic asymmetric carbon-carbon bond-forming reactions [J].
Sakthivel, K ;
Notz, W ;
Bui, T ;
Barbas, CF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (22) :5260-5267
[39]   Primary amino acid lithium salt as a catalyst for asymmetric Michael addition of isobutyraldehyde with β-nitroalkenes [J].
Sato, Atsushi ;
Yoshida, Masanori ;
Hara, Shoji .
CHEMICAL COMMUNICATIONS, 2008, (46) :6242-6244
[40]   Asymmetric 1,4-addition of diethylzinc to cyclic enones catalyzed by Cu(I)-chiral sulfonamide-thiophosphoramide ligands and lithium salts [J].
Shi, M ;
Zhang, W .
ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (04) :535-540