Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 67, Issue 6, Pages 1754-1759Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo001525c
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- NCI NIH HHS [CA-82169] Funding Source: Medline
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The Mitsunobu reaction typically proceeds with inversion of configuration at the hydroxyl center. However, with a series of hindered alcohols, the intramolecular version of the Mitsunobu reaction afforded exclusively the product of retention of configuration. A mechanistic rationale for this observation is discussed, wherein this atypical stereochemical outcome is attributed to steric congestion at the reaction center.
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