The Journal of Organic Chemistry

Diastereofacial selection in nitrile oxide cycloaddition reactions. The anti-directing effect of an allylic oxygen and some new results on the ring metalation of …

AP Kozikowski, AK Ghosh

文献索引：Kozikowski,, Alan P.; Ghosh, Arun K. Journal of Organic Chemistry, 1984 , vol. 49, # 15 p. 2762 - 2772

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被引用次数: 114

摘要

During our efforts to synthesize the ergot alkaloid paliclavine, we had the occasion to examine the extent of diastereoaelection which could be achieved in the addition of a nitrile oxide to a tethered olefin bearing an allylic asymmetric center.' Since the groups attached to this allylic site differed little in their steric or electronic makeup, it was not surprising to find that the extent of diastereoselection was small. Prompted by this initial experiment, we have begun to ...