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

doi:10.1021/acs.joc.6b01645

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 journal › Article › peer-review

6 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 language	English
Pages (from-to)	8464-8469
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	81
Issue number	18
DOIs	https://doi.org/10.1021/acs.joc.6b01645
Publication status	Published - 2016 Sept 16

Bibliographical note

Funding Information:
This work was supported by National Research Foundation of Korea (NRF) grants funded by the Korean Government (NRF- 2015R1D1A1A01057200 and NRF-20100020209). C.-H.C.thanks the financial support from an NRF grant funded by the Korean Government (NRF-2014-011165, Center for NewDirections in Organic Synthesis).

Publisher Copyright:
© 2016 American Chemical Society.

ASJC Scopus subject areas

Organic Chemistry

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

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.",

author = "Yoon, {Jung Min} and Lee, {Chun Young} and Jo, {Young In} and Cheon, {Cheol Hong}",

note = "Funding Information: This work was supported by National Research Foundation of Korea (NRF) grants funded by the Korean Government (NRF- 2015R1D1A1A01057200 and NRF-20100020209). C.-H.C.thanks the financial support from an NRF grant funded by the Korean Government (NRF-2014-011165, Center for NewDirections in Organic Synthesis). Publisher Copyright: {\textcopyright} 2016 American Chemical Society.",

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doi = "10.1021/acs.joc.6b01645",

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AU - Yoon, Jung Min

AU - Lee, Chun Young

AU - Jo, Young In

AU - Cheon, Cheol Hong

N1 - Funding Information: This work was supported by National Research Foundation of Korea (NRF) grants funded by the Korean Government (NRF- 2015R1D1A1A01057200 and NRF-20100020209). C.-H.C.thanks the financial support from an NRF grant funded by the Korean Government (NRF-2014-011165, Center for NewDirections in Organic Synthesis). Publisher Copyright: © 2016 American Chemical Society.

PY - 2016/9/16

Y1 - 2016/9/16

N2 - 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.

AB - 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.

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U2 - 10.1021/acs.joc.6b01645

DO - 10.1021/acs.joc.6b01645

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ER -

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

Abstract

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