CYCLOADDITIONS .44. A 2-STEP CONVERSION OF CARBONYL-COMPOUNDS INTO FUNCTIONALIZED 5-MEMBERED AND 6-MEMBERED RING THIOETHERS VIA INTRAMOLECULAR CYCLOADDITION

被引:30
作者
HASSNER, A
DEHAEN, W
机构
[1] Department of Chemistry, Bar-Ilan University, Ramat-Gan 52100, Israel
关键词
D O I
10.1021/jo00307a023
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reaction of aldehydes or ketones with nitromethane in the presence of unsaturated thiols led directly to unsaturated nitro sulfides 7,12,14, or 19. These compounds were converted by intramolecular nitrile oxide—olefin cycloaddition to tetrahydrothiopheno[3,4-c]isoxazoles 9, 10, 13, and 20 or to homologous thiopyrans 15 and 16 in some cases with a fair degree of stereoselectivity. Reduction of 9 or 13 led to tetrahydrothiophenes possessing stereoselectively placed amino alcohol functions, while desulfurization provided open-chain keto alcohol 24. © 1990, American Chemical Society. All rights reserved.
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页码:5505 / 5510
页数:6
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