Chemo- and enantioselective catalytic addition of propargyl chloride to aldehydes promoted by [Cr(Salen)] complexes

被引：49

作者：

Bandini, M ^{[1
]}

Cozzi, PG ^{[1
]}

Melchiorre, P ^{[1
]}

Tino, R ^{[1
]}

Umani-Ronchi, A ^{[1
]}

机构：

[1] Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy

来源：

TETRAHEDRON-ASYMMETRY | 2001年 / 12卷 / 07期

关键词：

D O I：

10.1016/S0957-4166(01)00182-3

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

We describe a full account of our study concerning the [Cr(Salen)]-catalysed addition of propargyl halides to aldehydes. Such a procedure allows the synthesis of enantiomerically enriched homopropargyl alcohols in satisfactory yields with enantiomeric excesses (e.e.s) up to 56%. The excellent chemoselectivity for homopropargyl l versus homoallenyl alcohol. represents a peculiar characteristic our process in comparison to other chromium-mediated propargylation reactions. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：1063 / 1069

页数：7

共 44 条

[1]

[Anonymous], CATALYTIC ASYMMETRIC

[2]

[Anonymous], 1993, HDB ENANTIOSELECTIVE

[3]

Bandini M, 1999, ANGEW CHEM INT EDIT, V38, P3357, DOI 10.1002/(SICI)1521-3773(19991115)38:22<3357::AID-ANIE3357>3.0.CO

[4]

2-W

[5] Cr(Salen)-catalyzed addition of 1,3-dichloropropene to aromatic aldehydes, a simple access to optically active vinyl epoxides [J].

Bandini, M ;

Cozzi, PG ;

Melchiorre, P ;

Morganti, S ;

Umani-Ronchi, A .

ORGANIC LETTERS, 2001, 3 (08) :1153-1155

[6] Enantioselective catalytic addition of allyl organometallic reagents to aldehydes promoted by [Cr(Salen)]: the hidden role played by weak Lewis acids in metallo-Salen promoted reactions [J].

Bandini, M ;

Cozzi, PG ;

Umani-Ronchi, A .

TETRAHEDRON, 2001, 57 (05) :835-843

[7]

Bandini M, 2000, ANGEW CHEM INT EDIT, V39, P2327, DOI 10.1002/1521-3773(20000703)39:13<2327::AID-ANIE2327>3.0.CO

[8]

2-9

[9] The asymmetric addition of trimethylsilyl cyanide to aldehydes catalyzed by chiral (salen)titanium complexes [J].

Belokon, YN ;

Caveda-Cepas, S ;

Green, B ;

Ikonnikov, NS ;

Krustalev, VN ;

Larichev, VS ;

Moscalenko, MA ;

North, M ;

Orizu, C ;

Tararov, VI ;

Tasinazzo, M ;

Timofeeva, GI ;

Yashkina, LV .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (16) :3968-3973

[10]

Bolm C, 1995, ANGEW CHEM INT EDIT, V34, P2640

← 1 2 3 4 5 →