Stereospecific synthesis of chiral tertiary alkyl-aryl ethers via Mitsunobu reaction with complete inversion of configuration

✍ Scribed by Yao-Jun Shi; David L. Hughes; James M. McNamara

• Publisher: Elsevier Science
• Year: 2003
• Tongue: French
• Weight: 124 KB
• Volume: 44
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(03)00728-7

✦ Synopsis

Mitsunobu reaction of chiral tertiary alcohol (S)-2 with phenol 3 provides the desired ether (R)-1 in moderate yields at elevated temperatures (80-100°C). The S N 2 displacement pathway is evident by complete inversion of the (S)-alcohol to (R)-ether.