An approach to the stereoselective synthesis of syn- and anti-1,3-diol derivatives. Retention of configuration in the Mitsunobu reaction.
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.
Ahn
Chuljin
C
Department of Chemistry and Biochemistry, University of Maryland, College Park, Maryland 20742, USA.
DeShong
Philip
P
D000438:Alcohols / Q000737:chemistry*; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods; D007783:Lactones / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D000438:Alcohols; D007783:Lactones; D009942:Organometallic Compounds