Recent Developments in Asymmetric Alkynylation of Imines

被引：92

作者：

Blay, G. ^{[1
]}

Monleon, A. ^{[1
]}

Pedro, J. R. ^{[1
]}

机构：

[1] Univ Valencia, Dept Quim Organ, Fac Quim, E-46100 Valencia, Spain

来源：

CURRENT ORGANIC CHEMISTRY | 2009年 / 13卷 / 15期

关键词：

HIGHLY ENANTIOSELECTIVE SYNTHESIS; COMPLEX-CATALYZED SYNTHESIS; POT 3-COMPONENT SYNTHESIS; AMINO-ACID DERIVATIVES; TERMINAL ALKYNES; DIRECT-ADDITION; ALKYNYLZINC REAGENTS; DIASTEREOSELECTIVE ADDITION; STEREOSELECTIVE-SYNTHESIS; RADICAL CYCLIZATION;

D O I：

10.2174/138527209789177734

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This review deals with the asymmetric alkynylation of imines (and iminium ions) to give chiral nonracemic propargylamines. Diastereoselective procedures involved the addition of metal alkynylides to chiral nonracemic imines derived from chiral amines or chiral carbonyl compounds. Enantioselective non-catalytic procedures have been achieved with the use of stoichiometric additives or alkynylboron reagents. Finally, catalytic addition of terminal alkynes or zinc acetylides has been carried out in the presence of chiral metal complexes, especially copper complexes as catalysts.

引用

页码：1498 / 1539

页数：42

共 109 条

[51]

Koradin C, 2002, ANGEW CHEM INT EDIT, V41, P2535, DOI 10.1002/1521-3773(20020715)41:14<2535::AID-ANIE2535>3.0.CO

[52]

2-M

[53] Reversal of diastereoselection in the addition of Grignard reagents to chiral 2-pyridyl tert-butyl (Ellman) sulfinimines [J].

Kuduk, SD ;

DiPardo, RM ;

Chang, RK ;

Ng, C ;

Bock, MG .

TETRAHEDRON LETTERS, 2004, 45 (35) :6641-6643

[54] FR-900130, A NOVEL AMINO-ACID ANTIBIOTIC .1. DISCOVERY, TAXONOMY, ISOLATION, AND PROPERTIES [J].

KURODA, Y ;

OKUHARA, M ;

GOTO, T ;

IGUCHI, E ;

KOHSAKA, M ;

AOKI, H ;

IMANAKA, H .

JOURNAL OF ANTIBIOTICS, 1980, 33 (02) :125-131

[55] A new method for the stereoselective synthesis of α-substituted serine amino acid analogues [J].

Lane, JW ;

Halcomb, RL .

ORGANIC LETTERS, 2003, 5 (22) :4017-4020

[56] A practical gold-catalyzed route to 4-substituted oxazolidin-2-ones from N-Boc propargylamines [J].

Lee, Eun-Sun ;

Yeom, Hyun-Suk ;

Hwang, Ji-Hyun ;

Shin, Seunghoon .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (21) :3503-3507

[57] Lewis base-catalyzed additions of alkynes using trialkoxysilylalkynes [J].

Lettan, RB ;

Scheidt, KA .

ORGANIC LETTERS, 2005, 7 (15) :3227-3230

[58] Chiral Cu(II) complex catalyzed enantioselective addition of phenylacetylene to N-aryl arylimines [J].

Liu, Bao ;

Huang, Ling ;

Liu, Juntao ;

Zhong, Yao ;

Li, Xingshu ;

Chan, Albert S. C. .

TETRAHEDRON-ASYMMETRY, 2007, 18 (24) :2901-2904

[59] The synthesis of chiral N-tosylatedaminoimine ligands and their application in enantioselective addition of phenylacetylene to imines [J].

Liu, Bao ;

Liu, Juntao ;

Jia, Xian ;

Huang, Ling ;

Li, Xingshu ;

Chan, Albert S. C. .

TETRAHEDRON-ASYMMETRY, 2007, 18 (09) :1124-1128

[60] Synthesis of enantiomerically pure N-tert-butanesulfinyl imines (tert-butanesulfinimines) by the direct condensation of tert-butanesulfinamide with aldehydes and ketones [J].

Liu, GC ;

Cogan, DA ;

Owens, TD ;

Tang, TP ;

Ellman, JA .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (04) :1278-1284

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