Asymmetric base-catalyzed Diels-Alder reaction of 3-hydroxy-2-pyrone with chiral acrylate derivatives

被引：36

作者：

Okamura, H ^{[1
]}

Morishige, K ^{[1
]}

Iwagawa, T ^{[1
]}

Nakatani, M ^{[1
]}

机构：

[1] Kagoshima Univ, Fac Sci, Dept Chem, Kagoshima 890, Japan

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 10期

关键词：

D O I：

10.1016/S0040-4039(97)10843-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In the presence of a cinchona alkaloid as a catalyst, the Diels-Alder reaction of 3-hydroxy-2-pyrone with chiral N-acryloyl oxazolidinone afforded a bicyclolactone adduct with high diastereoselectivities (up to 95%de) in almost quantitative yield. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：1211 / 1214

页数：4

共 11 条

[1] DIELS-ALDER CYCLOADDITIONS OF 2-PYRONES AND 2-PYRIDONES [J].

AFARINKIA, K ;

VINADER, V ;

NELSON, TD ;

POSNER, GH .

TETRAHEDRON, 1992, 48 (42) :9111-9171

[2]

EVANS DA, 1982, ALDRICHIM ACTA, V15, P318

[3] HIGH-PRESSURE CYCLOADDITIONS OF PYRONES - SYNTHESIS OF HIGHLY FUNCTIONALIZED 6-MEMBERED RINGS BY INHIBITION OF CARBON-DIOXIDE LOSS [J].

GLADYSZ, JA ;

LEE, SJ ;

TOMASELLO, JAV ;

YU, YS .

JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (25) :4170-4172

[4] DOUBLE ASYMMETRIC-SYNTHESIS AND A NEW STRATEGY FOR STEREOCHEMICAL CONTROL IN ORGANIC-SYNTHESIS [J].

MASAMUNE, S ;

CHOY, W ;

PETERSEN, JS ;

SITA, LR .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1985, 24 (01) :1-30

[5]

NARASAKA K, 1991, SYNTHESIS-STUTTGART, P1171

[6] SYNTHESIS OF A FULLY FUNCTIONALIZED CD RING-SYSTEM OF TAXOL [J].

NICOLAOU, KC ;

LIU, JJ ;

HWANG, CK ;

DAI, WM ;

GUY, RK .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (16) :1118-1120

[7] A BASE-CATALYZED DIELS-ALDER REACTION OF 3-HYDROXY-2-PYRONE [J].

OKAMURA, H ;

IWAGAWA, T ;

NAKATANI, M .

TETRAHEDRON LETTERS, 1995, 36 (33) :5939-5942

[8] Asymmetric base-catalyzed Diels-Alder reaction of 3-hydroxy-2-pyrone with N-methylmaleimide [J].

Okamura, H ;

Nakamura, Y ;

Iwagawa, T ;

Nakatani, M .

CHEMISTRY LETTERS, 1996, (03) :193-194

[9] ASYMMETRIC DIELS-ALDER REACTIONS - INVERSE ELECTRON DEMAND REACTIONS OF ESTERS OF 3-HYDROXYPYRAN-2-ONE WITH VINYL ETHERS - USE OF HIGH-PRESSURE TO AVOID DECARBOXYLATION OF ADDUCTS [J].

PRAPANSIRI, V ;

THORNTON, ER .

TETRAHEDRON LETTERS, 1991, 32 (27) :3147-3150

[10] CONVENIENT SYNTHESIS OF 3-METHOXYPHTHALIC ANHYDRIDE [J].

PROFITT, JA ;

JONES, T ;

WATT, DS .

SYNTHETIC COMMUNICATIONS, 1975, 5 (06) :457-460

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