Asymmetric addition of 1-ethynylcyclohexene to both aromatic and heteroaromatic ketones catalyzed by a chiral Schiff base-zinc complex

被引:27
作者
Wang, Quan
Zhang, Bangzhi
Hu, Guowen
Chen, Chao
Zhao, Qinyang
Wang, Rui [1 ]
机构
[1] Lanzhou Univ, Sch Life Sci, Dept Biochem & Mol Biol, Lanzhou 730000, Gansu, Peoples R China
[2] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Gansu, Peoples R China
[3] Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Gansu, Peoples R China
关键词
HIGHLY ENANTIOSELECTIVE ADDITION; PHENYLACETYLENE ADDITIONS; LITHIUM ACETYLIDE; ALKYNE ADDITIONS; PROCHIRAL KETONE; TERMINAL ALKYNES; ALDEHYDES; ALKYNYLATION; ALKYNYLZINC; ACETYLENES;
D O I
10.1039/b702069d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The evaluation of a chiral Schiff base ligand in the zinc-catalyzed asymmetric addition of 1-ethynylcyclohexene to both aromatic and heteroaromatic ketones is reported (with up to 83% enantioselectivity and up to 88% isolated yield).
引用
收藏
页码:1161 / 1163
页数:3
相关论文
共 43 条
[1]   A simple, mild, catalytic, enantioselective addition of terminal acetylenes to aldehydes [J].
Anand, NK ;
Carreira, EM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (39) :9687-9688
[2]   Mandelamide-zinc-catalyzed enantioselective alkyne addition to heteroaromatic aldehydes [J].
Blay, Gonzalo ;
Fernandez, Isabel ;
Marco-Aleixandre, Alicia ;
Pedro, Jose R. .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (17) :6674-6677
[3]   Efficient enantioselective additions of terminal alkynes and aldehydes under operationally convenient conditions [J].
Boyall, D ;
Frantz, DE ;
Carreira, EM .
ORGANIC LETTERS, 2002, 4 (15) :2605-2606
[4]   A new type of ligand derived from N-terminal protected dipeptides in enantioselective addition of phenylacetylene to aromatic ketones at room temperature [J].
Cai, Hua-qing ;
Chen, Chao ;
Liu, Lei ;
Ni, Jing-man ;
Wang, Rui .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2006, 253 (1-2) :86-91
[5]  
Chan KF, 2003, EUR J ORG CHEM, V2003, P82, DOI 10.1002/1099-0690(200301)2003:1<82::AID-EJOC82>3.0.CO
[6]  
2-X
[7]   Diastereoselective addition reactions of furyl aldehydes using chiral boronates as auxiliary: Application to the enantioselective synthesis of 2,3-disubstituted furyl alcohols [J].
Chan, KF ;
Wong, HNC .
ORGANIC LETTERS, 2001, 3 (25) :3991-3994
[8]   Low ligand loading, highly enantioselective addition of phenylacetylene to aromatic ketones catalyzed by Schiff-base amino alcohols [J].
Chen, Chao ;
Hong, Liang ;
Xu, Zhao-Qing ;
Liu, Lei ;
Wang, Rui .
ORGANIC LETTERS, 2006, 8 (11) :2277-2280
[9]   BINOL catalyzed enantioselective addition of titanium phenylacetylide to aromatic ketones [J].
Cozzi, PG ;
Alesi, S .
CHEMICAL COMMUNICATIONS, 2004, (21) :2448-2449
[10]   Enantioselective alkynylation of ketones catalyzed by Zn(salen) complexes [J].
Cozzi, PG .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (25) :2895-2898