Atropo- and diastereoselective construction of tetracyclic biphenylazepinium salts derived from aminoalcohols: Use as catalysts in enantioselective asymmetric epoxidation

Philip C. Bulman Page; Christopher A. Pearce; Yohan Chan; Phillip Parker; Benjamin R. Buckley; Gerasimos A. Rassias; Mark R.J. Elsegood

doi:10.1021/acs.joc.5b01157

Atropo- and diastereoselective construction of tetracyclic biphenylazepinium salts derived from aminoalcohols: Use as catalysts in enantioselective asymmetric epoxidation

Philip C. Bulman Page, Christopher A. Pearce, Yohan Chan, Phillip Parker, Benjamin R. Buckley, Gerasimos A. Rassias, Mark R.J. Elsegood

Chemistry of Materials and Catalysis

Research output: Contribution to journal › Article › peer-review

22 Citations (Scopus)

7 Downloads (Pure)

Abstract

A range of new biphenylazepinium salt organocatalysts effective for asymmetric epoxidation has been developed incorporating an additional substituted oxazolidine ring, and providing improved enantiocontrol in alkene epoxidation over the parent structure. Starting from enantiomerically pure aminoalcohols, tetracyclic iminium salts were obtained as single diastereoisomers through an atroposelective oxazolidine formation.

Original language	English
Pages (from-to)	8036-8045
Number of pages	10
Journal	Journal of Organic Chemistry
Volume	80
Early online date	23 Jul 2015
DOIs	https://doi.org/10.1021/acs.joc.5b01157
Publication status	Published - 21 Aug 2015

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10.1021/acs.joc.5b01157

Oxazolidine 16-07-15 JOCAccepted author manuscript, 691 KB

Cite this

Bulman Page, P. C., Pearce, C. A., Chan, Y., Parker, P., Buckley, B. R., Rassias, G. A., & Elsegood, M. R. J. (2015). Atropo- and diastereoselective construction of tetracyclic biphenylazepinium salts derived from aminoalcohols: Use as catalysts in enantioselective asymmetric epoxidation. Journal of Organic Chemistry, 80, 8036-8045. https://doi.org/10.1021/acs.joc.5b01157

Bulman Page, Philip C. ; Pearce, Christopher A. ; Chan, Yohan ; Parker, Phillip ; Buckley, Benjamin R. ; Rassias, Gerasimos A. ; Elsegood, Mark R.J. / Atropo- and diastereoselective construction of tetracyclic biphenylazepinium salts derived from aminoalcohols: Use as catalysts in enantioselective asymmetric epoxidation. In: Journal of Organic Chemistry. 2015 ; Vol. 80. pp. 8036-8045.

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abstract = "A range of new biphenylazepinium salt organocatalysts effective for asymmetric epoxidation has been developed incorporating an additional substituted oxazolidine ring, and providing improved enantiocontrol in alkene epoxidation over the parent structure. Starting from enantiomerically pure aminoalcohols, tetracyclic iminium salts were obtained as single diastereoisomers through an atroposelective oxazolidine formation.",

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Atropo- and diastereoselective construction of tetracyclic biphenylazepinium salts derived from aminoalcohols: Use as catalysts in enantioselective asymmetric epoxidation. / Bulman Page, Philip C.; Pearce, Christopher A.; Chan, Yohan; Parker, Phillip; Buckley, Benjamin R.; Rassias, Gerasimos A.; Elsegood, Mark R.J.

In: Journal of Organic Chemistry, Vol. 80, 21.08.2015, p. 8036-8045.

Research output: Contribution to journal › Article › peer-review

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AB - A range of new biphenylazepinium salt organocatalysts effective for asymmetric epoxidation has been developed incorporating an additional substituted oxazolidine ring, and providing improved enantiocontrol in alkene epoxidation over the parent structure. Starting from enantiomerically pure aminoalcohols, tetracyclic iminium salts were obtained as single diastereoisomers through an atroposelective oxazolidine formation.

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