An Approach to the Stereoselective Synthesis of syn- and anti-1,3-Diol Derivatives. Retention of Configuration in the Mitsunobu Reaction
The Journal of Organic Chemistry2002Vol. 67(6), pp. 1754–1759
Citations Over TimeTop 10% of 2002 papers
Abstract
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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