Spiro-fused Pyrrolidine, Piperidine, and Oxindole Scaffolds from Lactams

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• 作者：Christoph Hirschh盲user ; Jeremy S. Parker ; Matthew W. D. Perry ; Mairi F. Haddow ; Timothy Gallagher
• 刊名：Organic Letters
• 出版年：2012
• 出版时间：September 21, 2012
• 年：2012
• 卷：14
• 期：18
• 页码：4846-4849
• 全文大小：296K
• 年卷期：v.14,no.18(September 21, 2012)
• ISSN：1523-7052

文摘

Expedient routes to three classes of novel spiro-fused pyrrolidine, piperidine, and indoline heterocycle scaffolds are described. These three-dimensional frameworks, which conform to the 鈥渞ule of three鈥? are suitably protected to allow for site-selective manipulation and functionalization. Different modes of substrate control were explored, which allow for good to excellent levels of diastereoselectivity and dispense with the need for additional chiral reagents or catalysts. The concepts developed were applied in short, formal syntheses of (卤)-coerulescine and (卤)-horsfiline.