Highly diastereoselective hetero-Diels-Alder reactions of alkenyidihydrooxazoles as an approach to novel pyrimidine derivatives

被引：23

作者：

Elliot, MC

Kruiswijk, E

机构：

[1] Department of Chemistry, University of Wales Cardiff, Cardiff CF1 3TB

来源：

CHEMICAL COMMUNICATIONS | 1997年 / 23期

关键词：

D O I：

10.1039/a705571d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Chiral 2-alkenyldihydrooxazoles react with two equivalents of aryl and arylsulfonyl isocyanates to give chiral non-racemic dihydropyrimidone derivatives in high yield and with complete diastereocontrol.

引用

页码：2311 / 2312

页数：2

共 16 条

[1] ASYMMETRIC DIELS-ALDER REACTIONS WITH CHIRAL 1-AZADIENES [J].

BEAUDEGNIES, R ;

GHOSEZ, L .

TETRAHEDRON-ASYMMETRY, 1994, 5 (04) :557-560

[2] Synchronous or asynchronous? An ''experimental'' transition state from a direct comparison of experimental and theoretical kinetic isotope effects for a Diels-Alder reaction [J].

Beno, BR ;

Houk, KN ;

Singleton, DA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (41) :9984-9985

[3]

Boger D. L., 1987, HETERO DIELS ALDER M

[4]

Carruthers W, 1990, Cycloaddition Reactions in Organic Synthesis

[5] SEMIEMPIRICAL CALCULATIONS ON HETEROCUMULENE-HETERODIENE CYCLOADDITION REACTIONS - KETENE PLUS 1-AZABUTADIENE [J].

FABIAN, WMF ;

KOLLENZ, G .

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 1994, 7 (01) :1-8

[6] ALPHA,BETA-UNSATURATED OXAZOLINES, A POWERFUL TOOL IN ASYMMETRIC DIELS-ALDER CYCLOADDITIONS [J].

KOUKLOVSKY, C ;

POUILHES, A ;

LANGLOIS, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (18) :6672-6679

[7] CAPTODATIVE ALPHA,BETA-UNSATURATED OXAZOLINES AS DIENOPHILES IN THE ASYMMETRIC DIELS-ALDER REACTION [J].

LANGLOIS, Y ;

POUILHES, A .

TETRAHEDRON-ASYMMETRY, 1991, 2 (12) :1223-1230

[8]

MARCH J, 1992, ADV ORG CHEM, P978

[9] HETERO-DIELS-ALDER REACTION TRANSITION STRUCTURES - REACTIVITY, STEREOSELECTIVITY, CATALYSIS, SOLVENT EFFECTS, AND THE EXO-LONE-PAIR EFFECT [J].

MCCARRICK, MA ;

WU, YD ;

HOUK, KN .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (12) :3330-3343

[10] Diene-transmissive hetero-Diels-Alder reaction of cross-conjugated azatrienes: A novel and efficient method for the synthesis of ring-fused nitrogen heterocycles [J].

Saito, T ;

Kimura, H ;

Chonan, T ;

Soda, T ;

Karakasa, T .

CHEMICAL COMMUNICATIONS, 1997, (11) :1013-1014

← 1 2 →