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One‐Pot l ‐Proline‐Mediated Stereoselective α‐C(sp 2 )–H Fluorination of α,β‐Unsaturated Aldehydes through Methoxyfluorination–Elimination
Author(s) -
Zhou Jiadi,
Jiang Xinpeng,
Jin Can,
Guo Zhicheng,
Su Bin,
Su Weike
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201700622
Subject(s) - chemistry , stereoselectivity , hydrolysis , proline , cleavage (geology) , selectfluor , organic chemistry , stereochemistry , medicinal chemistry , amino acid , catalysis , biochemistry , geotechnical engineering , fracture (geology) , engineering
A one‐pot, two‐step l ‐proline‐mediated stereoselective α‐C(sp 2 )–H fluorination of α,β‐unsaturated aldehydes towards their corresponding ( Z )‐α‐fluoro‐α,β‐unsaturated aldehydes has been developed. The first step utilises Selectfluor as a fluorinating agent in CH 3 NO 2 /MeOH forming ( Z )‐α‐fluoro‐α,β‐unsaturated aldehydes and their corresponding dimethyl acetals through methoxyfluorination‐elimination. In the second step, water is added to promote the hydrolytic cleavage of the dimethyl acetals. The obtained ( Z )‐α‐fluoro‐α,β‐unsaturated aldehydes were smoothly reduced to the corresponding alcohols by using NaBH 4 .