Highly enantioselective alkynylation of aldehydes catalyzed by a readily available chiral amino alcohol-based ligand

被引：125

作者：

Jiang, B ^{[1
]}

Chen, ZL ^{[1
]}

Xiong, WN ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2002年 / 14期

关键词：

D O I：

10.1039/b203984b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new inexpensive chiral amino alcohol-based ligand, (1S,2S)-2-N, N-dimethylamino-1-(p-nitrophenyl)-3-(t-butyldimethylsilyloxy) propane-1-ol, was developed for the asymmetric alkynylation of aliphatic and aromatic aldehydes, to prepare the corresponding propargylic alcohols in high yields with up to 99% ee.

引用

页码：1524 / 1525

页数：2

共 25 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] 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

[3] 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

[4] 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

[5] EFFICIENT LIGANDS, CHIRAL 2-[2,2-DIMETHYL-1-(2-PYRIDYL)PROPOXY]-1,1-DIARYLETHANOLS FOR HIGHLY ENANTIOSELECTIVE ADDITION OF ALKYNYLZINC REAGENTS TO VARIOUS ALDEHYDES [J].

ISHIZAKI, M ;

HOSHINO, O .

TETRAHEDRON-ASYMMETRY, 1994, 5 (10) :1901-1904

[6]

Li Z, 1999, SYNTHESIS-STUTTGART, P1453

[7] Titanium-catalyzed enantioselective alkynylation of aldehydes [J].

Lu, G ;

Li, XS ;

Chan, WL ;

Chan, ASC .

CHEMICAL COMMUNICATIONS, 2002, (02) :172-173

[8] Chiral discrimination promoted by (1S,2S)-1-phenyl-2-amino-1,3-propanediol derivatives in the asymmetric reformatsky reaction [J].

Mastantuono, A ;

Pini, D ;

Rolfini, C ;

Salvadori, P .

CHIRALITY, 1995, 7 (07) :499-504

[9] New and stereospecific synthesis of allenes in a single step from propargylic alcohols [J].

Myers, AG ;

Zheng, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (18) :4492-4493

[10]

NOMINE G, 1968, B SOC CHIM FR, P3664

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