Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 74, Issue 21, Pages 8410-8413Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo901978y
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Funding
- National Science Foundation [CHE-0748058, CHE-0821501]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [0821501] Funding Source: National Science Foundation
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A three-step sequence to prepare polycyclic 2,5-dihydropyrroles from alpha-silyloxy ketones is presented. A Lewis acid-mediated ring fragmentation of cyclic gamma-sjlyloxy-beta-hydroxy-alpha-diazo esters provided tethered aldehyde ynoate intermediates which, when treated with amino acid silyl esters, underwent intramolecular azomethine ylide 1,3-dipolar cycloadditions. The 2,5-dihydropyrrole products were formed in good to excellent yield as single diastereomers.
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