Synthesis of Optically Pure 3,3′-Disubstituted-1,1′-Bi-6-Methoxy-2-Phenol (BIPhOL) Derivatives via Diastereomeric Resolution

Jung Min Yoon, Chun Young Lee, Young In Jo, Cheol-Hong Cheon

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

A new protocol for the enantioselective synthesis of 3,3′-disubstituted-1,1′-bi-6-methoxy-2-phenol (BIPhOL) derivatives is described. Diastereomeric resolution of racemic BIPhOL boronic acid using a boronic acid moiety as a resolving group generated two diastereomers and subsequent Suzuki-Miyaura coupling reaction of the resulting diastereomers with aryl halides provided BIPhOL derivatives without any loss of enantioselectivity. In addition, the absolute stereochemistry of chiral BIPhOL was determined by comparison of the optical rotation with the reported value.

Original languageEnglish
Pages (from-to)8464-8469
Number of pages6
JournalJournal of Organic Chemistry
Volume81
Issue number18
DOIs
Publication statusPublished - 2016 Sep 16

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Guaiacol
Boronic Acids
Derivatives
Optical rotation
Optical Rotation
Stereochemistry
Enantioselectivity

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis of Optically Pure 3,3′-Disubstituted-1,1′-Bi-6-Methoxy-2-Phenol (BIPhOL) Derivatives via Diastereomeric Resolution. / Yoon, Jung Min; Lee, Chun Young; Jo, Young In; Cheon, Cheol-Hong.

In: Journal of Organic Chemistry, Vol. 81, No. 18, 16.09.2016, p. 8464-8469.

Research output: Contribution to journalArticle

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