Zn(ODf)2:: preparation and application in asymmetric alkynylation of aldehydes

被引:48
作者
Chen, ZL [1 ]
Xiong, WN [1 ]
Jiang, B [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China
关键词
D O I
10.1039/b206868k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new Lewis acid, Zn(ODf)(2), was first prepared from commercially available 3,3,4,4-tetrafluoro[1,2] oxathietane 2,2-dioxide in four steps with 56% yields and also was applied to catalyze highly enantioselective alkynylation of aldehydes in the presence of ligand (1S,2S)-3-(tert-butyldimethylsilyloxyl)-2-N,N-dimethylamino-1-(p-nitrophenyl)propane-1-ol or ligand (-)-N-methylephedrine to afford the corresponding propargylic alcohols in high yields with up to 99% ee.
引用
收藏
页码:2098 / 2099
页数:2
相关论文
共 17 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]   METAL-COMPLEXES OF WEAKLY COORDINATING ANIONS - PRECURSORS OF STRONG CATIONIC ORGANOMETALLIC LEWIS-ACIDS [J].
BECK, W ;
SUNKEL, K .
CHEMICAL REVIEWS, 1988, 88 (07) :1405-1421
[3]   Enantioselective addition of 2-methyl-3-butyn-2-ol to aldehydes:: Preparation of 3-hydroxy-1-butynes [J].
Boyall, D ;
López, F ;
Sasaki, H ;
Frantz, D ;
Carreira, EM .
ORGANIC LETTERS, 2000, 2 (26) :4233-4236
[4]   KINETIC RESOLUTIONS OF CHIRAL UNSATURATED ALCOHOLS THAT CANNOT BE RESOLVED EFFICIENTLY VIA ENANTIOSELECTIVE EPOXIDATION [J].
BURGESS, K ;
JENNINGS, LD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (20) :7434-7436
[5]   ENANTIOSELECTIVE ESTERIFICATIONS OF UNSATURATED ALCOHOLS MEDIATED BY A LIPASE PREPARED FROM PSEUDOMONAS SP [J].
BURGESS, K ;
JENNINGS, LD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (16) :6129-6139
[6]   AN IMPROVED METHOD FOR SYNTHESIZING DIFLUOROMETHANESULFONIC ACID [J].
CHEN, QY ;
WU, SW .
JOURNAL OF FLUORINE CHEMISTRY, 1990, 47 (03) :509-514
[7]   A SIMPLE CONVENIENT METHOD FOR PREPARATION OF DIFLUOROMETHYL ETHERS USING FLUOROSULFONYLDIFLUORACETIC ACID AS A DIFLUOROCARBENE PRECURSOR [J].
CHEN, QY ;
WU, SW .
JOURNAL OF FLUORINE CHEMISTRY, 1989, 44 (03) :433-440
[8]   HIGHLY ENANTIOSELECTIVE ALKYNYLATION OF ALDEHYDES PROMOTED BY CHIRAL OXAZABOROLIDINES [J].
COREY, EJ ;
CIMPRICH, KA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (07) :3151-3152
[9]   Facile enantioselective synthesis of propargylic alcohols by direct addition of terminal alkynes to aldehydes [J].
Frantz, DE ;
Fässler, R ;
Carreira, EM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (08) :1806-1807
[10]   The discovery of novel reactivity in the development of C-C bond-forming reactions:: In situ generation of zinc acetylides with ZnII/R3N [J].
Frantz, DE ;
Fässler, R ;
Tomooka, CS ;
Carreira, EM .
ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (06) :373-381