Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 77, Issue 21, Pages 9910-9914Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo301944t
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- NIH (National Institute of General Medical Sciences) [R01GM092870]
- National Science Foundation [CHE-0821501]
- INBRE Program of the National Institute of General Medical Sciences (NIGMS), National Institutes of Health (NIH) [8P20GM103449]
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A series of gamma-silyloxy-beta-hydroxy-alpha-diazocarbonyl compounds were prepared as fragmentation substrates to probe the hypothesis that steric interactions between the diazo ester and adjacent silyloxy group can play an important role in determining the success of fragmentations; Proper stereoelectronic alignment of the diazo ester and the departing hydroxyl group is necessary for productive fragmentation to occur.
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