Tandem reactions catalyzed by lanthanide iodides.: Part 1:: Tandem Mukaiyama-Michael iminoaldol reactions

被引：24

作者：

Jaber, N ^{[1
]}

Assié, M ^{[1
]}

Fiaud, JC ^{[1
]}

Collin, J ^{[1
]}

机构：

[1] Univ Paris 11, ICMMO, Lab Catalyse Mol, UMR 8075, F-91405 Orsay, France

来源：

TETRAHEDRON | 2004年 / 60卷 / 13期

关键词：

samarium diiodide; catalysis; imines; Michael reaction; Mannich reaction; tandem reaction;

D O I：

10.1016/j.tet.2004.01.081

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Samarium diiodide, as well as lanthanide triiodides catalyze a one-pot procedure allowing to perform sequentially the Mukaiyama-Michael addition of a ketene silyl acetal on a cyclic alpha,beta-unsaturated ketone, followed by the addition of a glyoxylic, aromatic or heteroaromatic imine. According to the nature of the silyl group the adducts resulting from this tandem process are isolated as ketones or as enoxysilanes. The presence of a coordinating group on the imine increases the rate of the reaction. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：3075 / 3083

页数：9

共 90 条

[1]

Akiyama T, 1998, SYNLETT, P273

[2] Tandem enantioselective conjugate addition-cyclopropanation. Application to natural products synthesis [J].

Alexakis, A ;

March, S .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (25) :8753-8757

[3] Tandem enantioselective conjugate addition: Electrophile trapping reactions. application in the formation of syn or anti aldols [J].

Alexakis, A ;

Trevitt, GP ;

Bernardinelli, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (18) :4358-4359

[4] Yb(OTf)(3)-Catalyzed one-pot synthesis of beta-lactams from silyl ketene thioacetals by a two- or a three-component reaction [J].

Annunziata, R ;

Cinquini, M ;

Cozzi, F ;

Molteni, V ;

Schupp, O .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (23) :8293-8296

[5] Catalytic enantioselective synthesis of (-)-prostaglandin E1 methyl ester based on a tandem 1,4-addition-aldol reaction [J].

Arnold, LA ;

Naasz, R ;

Minnaard, AJ ;

Feringa, BL .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (21) :7244-7254

[6] Three component synthesis of homoallylic amines. Efficient catalysis by lanthanum triflate/benzoic acid [J].

Aspinall, HC ;

Bissett, JS ;

Greeves, N ;

Levin, D .

TETRAHEDRON LETTERS, 2002, 43 (02) :323-325

[7] Sequential one-pot InBr3-catalyzed 1,4-then 1,2-nucleophilic addition to enones [J].

Bandini, M ;

Cozzi, PG ;

Giacomini, M ;

Melchiorre, P ;

Selva, S ;

Umani-Ronchi, A .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (11) :3700-3704

[8] A three-component coupling protocol for the synthesis of substituted hexahydropyrrolo[3,2-c]quinolines [J].

Batey, RA ;

Simoncic, PD ;

Lin, D ;

Smyj, RP ;

Lough, AJ .

CHEMICAL COMMUNICATIONS, 1999, (07) :651-652

[9] RECENT ADVANCES IN THE USE OF TANDEM REACTIONS FOR ORGANIC-SYNTHESIS [J].

BUNCE, RA .

TETRAHEDRON, 1995, 51 (48) :13103-13159

[10] Lanthanide iodides, a new family of efficient Lewis acid catalysts [J].

Collin, J ;

Giuseppone, N ;

Van de Weghe, P .

COORDINATION CHEMISTRY REVIEWS, 1998, 178 :117-144

← 1 2 3 4 5 6 7 8 9 →