Reactions of zinc enolates derived from 1-aryl-2,2-di-bromoalkanones with 2-acyl-3H-benzo[f]chromen-3-ones, 6-bromo-2-oxochromene-3-carboxamides, and 3-oxo-3H-benzo[f]chromene-2-carboxamides

被引：12
|
作者：
Shchepin, VV
Kalyuzhnyi, MM
Silaichev, PS
Russkikh, NY
Shchepin, RV
Ezhikova, MA
Kodess, MI
机构：
[1] Perm State Univ, Perm 614990, Russia
[2] Russian Acad Sci, Inst Organ Synth, Ural Div, Ekaterinburg 620219, Russia
来源：
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 40卷 / 09期
基金：
俄罗斯基础研究基金会;
关键词：
Zinc; Organic Chemistry; Enolates; Morpholino; High Stereoselectivity;
D O I：
10.1007/s11178-005-0019-z
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Zinc enolates derived from substituted 1-aryl-2,2-dibromoalkanones reacted with 2-acyl-3H-benzo-[f]chromen-3-ones to give 1-alkyl-1-aroyl-1a-acyl-1a,9c-dihydro-1H-3-oxacyclopropa[c]phenanthren-2-ones which were formed as a single stereoisomer. Reactions of the same zinc enolates with 6-bromo-2-oxochromene-3-carboxamides (piperidides and morpholides) afforded 1-aroyl-6-bromo-1-alkyl-1a-piperidino(morpholino)carbonyl-la,7b-dihydrocyclopropa[c]chromen-2-ones with high stereoselectivity. Likewise, 1-benzoyl-1-methyl-1a-morpholinocarbonyl-1a,9c-dihydro-1H-3-oxacyclopropa[c]phenanthren-2-one was obtained by reaction with 3-oxo-3H-benzo[f]chromene-2-carboxylic acid morpholide.
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页码：1353 / 1358
页数：6
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