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- Publisher
- Wiley
- Copyright
- Copyright © 2013 Wiley Subscription Services, Inc., A Wiley Company
- ISSN
- 2193-5807
- eISSN
- 2193-5815
- DOI
- 10.1002/ajoc.201300171
- Publisher site
- See Article on Publisher Site
Abstract
The fluorous prolinol methyl ether was prepared through the perfluorohexylethylation of (S)‐1‐tert‐butyl 2‐methyl pyrrolidine‐1,2‐dicarboxylate using commercially available perfluorohexylethyl iodide, methylation, and deprotection in three steps in 19 % overall yield. In the asymmetric Michael addition reaction of nitrostyrene with propanal, the diastereoselectivity (syn/anti=92:8) with the prepared fluorous prolinol methyl ether was much higher than that (syn/anti=87–80:13–20) with nonfluorinated prolinol methyl ethers that have two n‐octyl groups or two phenyl groups in place of perfluorohexylethyl groups.
Journal
Asian Journal of Organic Chemistry – Wiley
Published: Dec 1, 2013
Keywords: ; ; ; ;