Marsh, B.J., Adams, H., Barker, M.D. et al. (2 more authors) (2014) Enantioselective Catalytic Desymmetrization of Maleimides by Temporary Removal of an Internal Mirror Plane and Stereoablative Over-reduction: Synthesis of (R)-Pyrrolam A. Organic Letters, 16 (14). 3780 - 3783. ISSN 1523-7060
Abstract
A highly enantioselective (>95% ee) strategy to affect the desymmetrization of a maleimide has been performed by temporary attachment to an anthracene template followed by asymmetric reduction with an oxazaborolidine catalyst. A stereoablative over-reduction process was partially responsible for the high levels of enantioselectivity. Exemplification of the strategy by stereoselective functionalization and retro-Diels−Alder reaction provided the natural product pyrrolam A.
Metadata
Authors/Creators: |
|
||||
---|---|---|---|---|---|
Copyright, Publisher and Additional Information: | © 2014 The Author(s). This is an Open Access article distributed under the terms of the Creative Commons Attribution Licence (http://creativecommons.org/licenses/by/3.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. | ||||
Dates: |
|
||||
Institution: | The University of Sheffield | ||||
Academic Units: | The University of Sheffield > Faculty of Science (Sheffield) > Department of Chemistry (Sheffield) | ||||
Funding Information: |
|
||||
Depositing User: | Symplectic Sheffield | ||||
Date Deposited: | 11 Dec 2014 09:53 | ||||
Last Modified: | 11 Dec 2014 09:53 | ||||
Published Version: | http://dx.doi.org/10.1021/ol5016702 | ||||
Status: | Published | ||||
Publisher: | American Chemical Society | ||||
Refereed: | Yes | ||||
Identification Number: | https://doi.org/10.1021/ol5016702 |