Please use this identifier to cite or link to this item: https://doi.org/10.1002/ajoc.201300211
Title: Highly enantioselective preparation of fluorinated phosphonates by michael addition of α-fluoro-β-ketophosphonates to nitroalkenes
Authors: Kwiatkowski, J.
Lu, Y. 
Keywords: Asymmetric synthesis
Michael addition
Organofluorine
Phosphate mimetics
α-fluoro-β-ketophosphonates
Issue Date: 2014
Citation: Kwiatkowski, J., Lu, Y. (2014). Highly enantioselective preparation of fluorinated phosphonates by michael addition of α-fluoro-β-ketophosphonates to nitroalkenes. Asian Journal of Organic Chemistry 3 (4) : 458-461. ScholarBank@NUS Repository. https://doi.org/10.1002/ajoc.201300211
Abstract: Fluorinated phosphonates are excellent surrogates of phosphates, outperforming the latter in terms of hydrolytic stability in biological systems while retaining similar activities. However, methods for preparing chiral fluorinated phosphonates are very limited. In this report, racemic α-fluoro-β-ketophosphonates were used in stereoselective Michael addition to nitroalkenes promoted by trifunctional thiourea organocatalyst. Highly functionalised α-fluoro-β-keto-γ-nitrophosphonates were obtained in high yields of 84-99% with excellent stereochemical control (96-99% ee and 3:1-34:1 d.r.). © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Source Title: Asian Journal of Organic Chemistry
URI: http://scholarbank.nus.edu.sg/handle/10635/93945
ISSN: 21935807
DOI: 10.1002/ajoc.201300211
Appears in Collections:Staff Publications

Show full item record
Files in This Item:
There are no files associated with this item.

SCOPUSTM   
Citations

14
checked on Jun 19, 2018

WEB OF SCIENCETM
Citations

14
checked on Jun 11, 2018

Page view(s)

28
checked on Mar 12, 2018

Google ScholarTM

Check

Altmetric


Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.