The first use of chiral oxazoline ligands in the highly enantioselective diethylzinc addition to diphenylphosphinoyl imines

被引：37

作者：

Zhang, XM

Lin, WQ

Gong, LZ ^{[1
]}

Mi, AQ

Cui, X

Jiang, YZ

Choi, MCK

Chan, ASC

机构：

[1] Chinese Acad Sci, Chengdu Inst Organ Chem, Union Lab Asymmetr Synth, Chengdu 610041, Peoples R China

[2] Hong Kong Polytech Univ, Open Lab Chirotechnol, Hong Kong, Hong Kong, Peoples R China

[3] Hong Kong Polytech Univ, Dept Appl Biol & Chem Technol, Hong Kong, Hong Kong, Peoples R China

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 08期

基金：

中国国家自然科学基金;

关键词：

diethylzinc addition; imines; oxazolines;

D O I：

10.1016/S0040-4039(02)00014-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of chiral oxazolines, which had been conveniently prepared from commercially available (1S, 2S)-2-amino-1-phenylpropane-1,3-diol, was applied in the diethylzine addition to diphenylphosphinoyl imines to give high yields of 68-84% and excellent e.e values of 90-93%. (C) 2002 Published by Elsevier Science Ltd.

引用

收藏

页码：1535 / 1537

页数：3

相关论文

共 29 条

[11] Progress in the Mitsunobu reaction. A review [J].

Hughes, DL .

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1996, 28 (02) :127-164

[12]

Jacques J., 1981, Enantiomers, Racemates and Resolutions

[13] Highly enantioselective addition of diethylzinc to diphenylphosphinoyl imines under dual amino alcohol/halosilane mediation [J].

Jimeno, C ;

Reddy, KS ;

Solà, L ;

Moyano, A ;

Pericàs, MA ;

Riera, A .

ORGANIC LETTERS, 2000, 2 (20) :3157-3159

[14]

Johansson A., 1995, CONTEMP ORG SYNTH, V2, P393

[15] Catalytic enantioselective addition to imines [J].

Kobayashi, S ;

Ishitani, H .

CHEMICAL REVIEWS, 1999, 99 (05) :1069-1094

[16] THE USE OF DIETHYL AZODICARBOXYLATE AND TRIPHENYLPHOSPHINE IN SYNTHESIS AND TRANSFORMATION OF NATURAL-PRODUCTS [J].

MITSUNOBU, O .

SYNTHESIS-STUTTGART, 1981, (01) :1-28

[17] THE INFLUENCE OF ATROPISOMERISM AND CHIRAL CENTER ON THE BIOLOGICAL-ACTIVITY OF METOLACHLOR [J].

MOSER, H ;

RIHS, G ;

SAUTER, H .

ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 1982, 37 (04) :451-462

[18]

POELERT MA, 1994, RECL TRAV CHIM PAY B, V113, P355

[19] Enantioselective synthesis of arylamines through Zr-catalyzed addition of dialkylzincs to imines. Reaction development by screening of parallel libraries [J].

Porter, JR ;

Traverse, JF ;

Hoveyda, AH ;

Snapper, ML .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (05) :984-985

[20] A concise synthesis of (R)-(+)-phenylalaninol from (1S,2S)-(+)-thiomicamine [J].

Rozwadowska, MD .

TETRAHEDRON-ASYMMETRY, 1998, 9 (09) :1615-1618