Highly stereoselective hetero Diels-Alder reactions of chiral 3-(p-tolylsulfinyl)-2-furaldehyde with Danishefsky's diene promoted by a lanthanoid Lewis acid

被引：22

作者：

Arai, Y ^{[1
]}

Masuda, T ^{[1
]}

Masaki, Y ^{[1
]}

Shiro, M ^{[1
]}

机构：

[1] RIGAKU CORP,AKISHIMA,TOKYO 196,JAPAN

来源：

TETRAHEDRON-ASYMMETRY | 1996年 / 7卷 / 04期

关键词：

D O I：

10.1016/0957-4166(96)00126-7

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Hetero Diels-Alder reactions of optically active 3-(p-tolylsulfinyl)-2-furaldehyde with 1-methoxy-3-(trimethylsilyloxy)-buta-1,3-diene (Danishefsky's diene) in the presence of a Lewis acid has been examined. The reaction in the presence of 1.0 equiv, of Ln(OTf)(3) (Ln = Yb, Nd and Sm) followed by acidic workup produced in good yields (68-88%) the hetero Diels-Alder adduct with high diastereoisomeric excesses (93-98% d.e.'s), whereas in the presence of an NMR shift reagent, tris(2,2,6,6-tetramethyl-3,5-heptanedionate)europium [Eu(thd)(3)] the corresponding diastereoisomer was obtained as the major adduct in excellent yield with 77% d.e. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：1199 / 1204

页数：6

共 26 条

[1] [Anonymous], SULFUR REPORTS
[2] DIASTEREOSELECTIVE ADDITION OF ALLYLTRIPHENYL-STANNANE TO 3-SULFINYLFURFURAL MEDIATED BY TITANIUM(IV) TETRACHLORIDE AND TIN(IV) TETRACHLORIDE
ARAI, Y
MASUDA, T
MASAKI, Y
KOIZUMI, T
[J]. HETEROCYCLES, 1994, 38 (08) : 1751 - 1756
[3] CHIRAL INDUCTION IN THE CYCLOCONDENSATION OF ALDEHYDES WITH SILOXYDIENES
BEDNARSKI, M
MARING, C
DANISHEFSKY, S
[J]. TETRAHEDRON LETTERS, 1983, 24 (33) : 3451 - 3454
[4] INTERACTIVITY OF CHIRAL CATALYSTS AND CHIRAL AUXILIARIES IN THE CYCLOADDITION OF ACTIVATED DIENES WITH ALDEHYDES - A SYNTHESIS OF L-GLUCOSE
BEDNARSKI, M
DANISHEFSKY, S
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (22) : 7060 - 7067
[5] ON THE INTERACTIVITY OF CHIRAL AUXILIARIES WITH CHIRAL CATALYSTS IN THE HETERO DIELS-ALDER REACTION - A NEW ROUTE TO L-GLYCOLIPIDS
BEDNARSKI, M
DANISHEFSKY, S
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (23) : 6968 - 6969
[6] BEDNARSKI M, 1988, J AM CHEM SOC, V110, P310
[7] BOGER DL, 1987, HETERO DIELSALDER ME, P105
[8] APPLICATIONS OF SULFOXIDES TO ASYMMETRIC-SYNTHESIS OF BIOLOGICALLY-ACTIVE COMPOUNDS
CARRENO, MC
[J]. CHEMICAL REVIEWS, 1995, 95 (06) : 1717 - 1760
[9] 1,5-ASYMMETRIC INDUCTIONS IN THE REACTIONS OF 2-(2',3',4',6'-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSYLOXY)BENZALDEHYDE WITH DANISHEFSKYS DIENE
COUSINS, RPC
CURTIS, ADM
DING, WC
STOODLEY, RJ
[J]. TETRAHEDRON LETTERS, 1995, 36 (47) : 8689 - 8692
[10] VARIATIONS IN THE STEREOCHEMISTRY OF THE BORON-TRIFLUORIDE MEDIATED CYCLOCONDENSATION REACTION OF ALDEHYDES WITH SILOXY DIENES
DANISHEFSKY, S
CHAO, KH
SCHULTE, G
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (23) : 4650 - 4652

← 1 2 3 →