One-pot synthesis of silyl-substituted dihydro-2H-pyran-2-ols from 3-phenyldimethylsilyl-1-diethylaminopropyne and epoxides

被引：3

作者：

Schabbert, S ^{[1
]}

Schaumann, E ^{[1
]}

机构：

[1] Tech Univ Clausthal, Inst Organ Chem, D-38678 Clausthal Zellerfeld, Germany

来源：

TETRAHEDRON | 1999年 / 55卷 / 05期

关键词：

carbanions; ynamines; oxiranes; cyclization;

D O I：

10.1016/S0040-4020(98)01118-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of lithiated 3-phenyldimethylsilyl-1-diethylaminopropyne 2 with oxiranes 3 affords silyl-substituted dihydro-2H-pyran-2-ols 6 and / or 7. The intermediates alpha,beta-unsaturated 5-hydroxy aldehydes 5 can be isolated, but cyclize easily to the 6-membered oxacycles. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：1271 / 1276

页数：6

共 10 条

[1] Brandsma L, 1988, PREPARATIVE ACETYLEN
[2] COLLARDMOTTE J, 1986, TOP CURR CHEM, V130, P89
[3] A METHOD FOR EXTENSION OF CARBON CHAINS BY GAMMA-ALKYLATION OF METALATED ALPHA,BETA-YNAMINES
COREY, EJ
CANE, DE
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (10) : 3405 - &
[4] FICINI J, 1965, B SOC CHIM FR, P2787
[5] Himbert G, 1997, SYNTHESIS-STUTTGART, P293
[6] HIMBERT G, 1993, HOUBENWEYL METHODE E, V15, P3267
[7] PENNANEN SI, 1984, FINN CHEM LETT, P95
[8] 3-TRIMETHYLSILYL-1-DIETHYLAMINOPROPYNE
PENNANEN, SI
[J]. SYNTHETIC COMMUNICATIONS, 1980, 10 (05) : 373 - 379
[9] THE LITHIATED 3-TRIMETHYLSILYL-1-DIETHYLAMINOPROPYNE
PENNANEN, SI
[J]. SYNTHETIC COMMUNICATIONS, 1982, 12 (03) : 209 - 212
[10] VIEHE HG, 1967, ANGEW CHEM, V79, P744, DOI DOI 10.1002/ANIE.196707671

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