Novel reactivity of stabilized methylenetributylphosphorane: A new mitsunobu reagent

✍ Scribed by Tetsuto Tsunoda; Fumie Ozaki; Shô Itô

• Publisher: Elsevier Science
• Year: 1994
• Tongue: French
• Weight: 245 KB
• Volume: 35
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)73326-0

✦ Synopsis

Absbract= Cy~~ethylenet~~tyiphospho~e

was shown to mediate the direct condensation of alcohols with O-and ~-n~leo~~~~. A secondary aicohoi. Z-octanoi, reacted ~tjsfacto~~y with Wahlen inversion of it.3 carbinyl carbon.

Tbe Mitsunobu ma&on is a very versatile method for the aikylation with alcohols of various nuch?ophites {or acids, HA), utiiizing the redox system of diethyl azodicarboxyiate (DEN)-t~phenylp~sphi~ (TPP) (eq. 1): Wi~ut any p~~u~si~ activation of the alcohols, it is a unique ~ky~~on reaction and widely applied to various phases of organic synthesis, DEAD

R-OH