INTERMOLECULAR AND INTRAMOLECULAR HETERO-DIELS-ALDER REACTIONS .39. INFLUENCE OF PHENYLTHIO AND ALKYLTHIO SUBSTITUENTS ON THE REACTIVITY OF 1-OXA-1,3-BUTADIENES IN HETERO-DIELS-ALDER REACTIONS

被引：13

作者：

TIETZE, LF

FENNEN, J

WICHMANN, J

机构：

[1] Institut Für Organische Chemie, Universität Göttingen, Göttingen, W-3400

来源：

CHEMISCHE BERICHTE-RECUEIL | 1992年 / 125卷 / 06期

关键词：

ENAMINO KETONES; 1,4-THIAZINES; HETERO-DIELS-ALDER REACTIONS; PYRANS; DIHYDRO; CALCULATIONS; SEMIEMPIRICAL;

D O I：

10.1002/cber.19921250629

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The synthesis of the cyclic enamino ketones 1-3 bearing an alkylthio or an phenylthio group and their reactivity in hetero Diels-Alder reactions with enol ethers is described. Only compound 3 with an phenylthio group undergoes a cycloaddition with 16a-d to afford the diastereomeric adducts 17a-d and 18a-d. To estimate the activation by a phenylthio and alkylthio group semiempirical PM3/RHF calculations of the frontier orbital energies and coefficients of different enamine carbaldehydes have been performed.

引用

页码：1507 / 1511

页数：5

共 18 条

[1]

APPARAO S, 1987, SYNTHESIS-STUTTGART, V896, P900

[2] INTERMOLECULAR AND INTRAMOLECULAR HETERO DIELS-ALDER REACTIONS .26. DIASTEREOSELECTIVITY AND KINETICS OF INTERMOLECULAR HETERO DIELS-ALDER REACTIONS UNDER HIGH-PRESSURE - A SIGNIFICANT PRESSURE-INDUCED INCREASE IN STEREOSELECTIVITY [J].