Faggyas, R. J., Calder, E. D.D., Wilson, C. and Sutherland, A. (2017) One-pot asymmetric synthesis of alkylidene 1-alkylindan-1-ols using Brønsted acid and palladium catalysis. Journal of Organic Chemistry, 82(21), pp. 11585-11593. (doi: 10.1021/acs.joc.7b02287) (PMID:28985675)
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Abstract
A one-pot catalytic enantioselective allylboration/Mizoroki–Heck reaction of 2-bromoaryl ketones has been developed for the asymmetric synthesis of 3-methyleneindanes bearing a tertiary alcohol center. Brønsted acid-catalyzed allylboration with a chiral BINOL derivative was followed by a palladium-catalyzed Mizoroki–Heck cyclization, resulting in selective formation of the exo-alkene. This novel protocol provides a concise and scalable approach to 1-alkyl-3-methyleneindan-1-ols in high enantiomeric ratios (up to 96:4 er). The potential of these compounds as chiral building blocks was demonstrated with efficient transformation to optically active diol and amino alcohol scaffolds.
| Item Type: | Articles |
|---|---|
| Status: | Published |
| Refereed: | Yes |
| Glasgow Author(s) Enlighten ID: | Wilson, Dr Claire and Sutherland, Professor Andrew and Faggyas, Réka |
| Authors: | Faggyas, R. J., Calder, E. D.D., Wilson, C., and Sutherland, A. |
| College/School: | College of Science and Engineering > School of Chemistry |
| Journal Name: | Journal of Organic Chemistry |
| Publisher: | American Chemical Society |
| ISSN: | 0022-3263 |
| ISSN (Online): | 1520-6904 |
| Published Online: | 06 October 2017 |
| Copyright Holders: | Copyright © 2017 American Chemical Society |
| First Published: | First published in Journal of Organic Chemistry 82(21): 11585-11593 |
| Publisher Policy: | Reproduced under a Creative Commons License |
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