Reversal of stereoselectivity of Mg(II) catalysed 1,3-dipolar cycloaddition.: Acceleration of cycloaddition by microwave irradiation.

被引：35

作者：

Micúch, P

Fisera, L ^{[1
]}

Cyranski, MK

Krygowski, TM

机构：

[1] Slovak Univ Technol Bratislava, Dept Organ Chem, Bratislava 81237, Slovakia

[2] Univ Warsaw, Dept Chem, PL-02093 Warsaw, Poland

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 01期

关键词：

cycloadditions; diastereoselection; nitrile oxides; microwave heating;

D O I：

10.1016/S0040-4039(98)80049-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1,3-Dipolar cycloadditions of mesitonitrile oxide to Baylis-Hillman adducts (beta-hydroxy-alpha-methylene esters) proceed regioselectively in good yields. Addition of a Grignard reagent reverses the diastereoselectivity of the cycloaddition. Microwave irradiation strongly accelerates the reaction with only a small effect on its diastereoisomeric excess. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：167 / 170

页数：4

相关论文

共 13 条

[1] 1,3-DIPOLAR CYCLOADDITIONS TO BAYLIS-HILLMAN ADDUCTS - RATIONALE FOR THE OBSERVED DIASTEREOSELECTIVITY [J].

ANNUNZIATA, R ;

BENAGLIA, M ;

CINQUINI, M ;

COZZI, F ;

RAIMONDI, L .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (15) :4697-4706

[2] SYNTHETIC OPPORTUNITIES OFFERED BY ANTI ALPHA-METHYLENE-BETA-HYDROXY-GAMMA-ALKOXY ESTERS - STEREOSELECTIVE REACTIONS AT THE DOUBLE-BOND [J].

BERNARDI, A ;

BERETTA, MG ;

COLOMBO, L ;

GENNARI, C ;

POLI, G ;

SCOLASTICO, C .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (23) :4442-4447

[3]

CARRUTHERS W, 1990, CYCLOADDITION REACTI, P285

[4]

FOUCAUD A, 1989, B SOC CHIM FR, P403

[5] STEREOSELECTIVE NITRILE OXIDE CYCLO-ADDITIONS TO CHIRAL ALLYL ETHERS AND ALCOHOLS - THE INSIDE ALKOXY EFFECT [J].

HOUK, KN ;

MOSES, SR ;

WU, YD ;

RONDAN, NG ;

JAGER, V ;

SCHOHE, R ;

FRONCZEK, FR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (13) :3880-3882

[6] RECENT ADVANCES IN SYNTHETIC APPLICATIONS OF NITRILE OXIDE CYCLOADDITION (1981-1989) [J].

KANEMASA, S ;

TSUGE, O .

HETEROCYCLES, 1990, 30 (01) :719-736

[7] 1ST SUCCESSFUL METAL COORDINATION CONTROL IN 1,3-DIPOLAR CYCLOADDITIONS - HIGH-RATE ACCELERATION AND REGIOCONTROL AND STEREOCONTROL OF NITRILE OXIDE CYCLOADDITIONS TO THE MAGNESIUM ALKOXIDES OF ALLYLIC AND HOMOALLYLIC ALCOHOLS [J].

KANEMASA, S ;

NISHIUCHI, M ;

KAMIMURA, A ;

HORI, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (06) :2324-2339

[8] LEWIS-ACID COORDINATED NITRILE OXIDE AND NITRILE IMINE 1,3-DIPOLES - SYN-SELECTIVE CYCLOADDITIONS TO 2-(1-HYDROXYALKYL)ACRYLATES [J].

KANEMASA, S ;

KOBAYASHI, S .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1993, 66 (09) :2685-2693

[9]

Lang S. A. J., 1984, COMPREHENSIVE HETERO, V6

[10]

Page PCB, 1997, TETRAHEDRON, V53, P7365