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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: John Wiley and Sons
Year: 2003
Weight: 78 KB
Volume: 34
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.200330110

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✦ Synopsis

Abstract

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📜 SIMILAR VOLUMES

Stereospecific synthesis of chiral terti

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

✍ Yao-Jun Shi; David L. Hughes; James M. McNamara 📂 Article 📅 2003 🏛 Elsevier Science 🌐 French ⚖ 124 KB

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.