Premium
Stereoselective Synthesis of ( Z )‐4‐(2‐Bromovinyl)benzene‐sulfonyl Azide and Its Synthetic Utility for the Transformation to ( Z )‐ N ‐[4‐(2‐Bromovinyl)benzenesulfonyl]imidates
Author(s) -
Zhang Wensheng,
Kuang Chunxiang,
Yang Qing
Publication year - 2009
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.200990291
Subject(s) - chemistry , azide , stereoselectivity , decarboxylation , sulfonyl , benzene , phenols , transformation (genetics) , stereochemistry , medicinal chemistry , combinatorial chemistry , organic chemistry , catalysis , alkyl , biochemistry , gene
A novel method for the stereoselective synthesis of ( Z )‐4‐(2‐bromovinyl)benzenesulfonyl azide by simultaneous azidation and debrominative decarboxylation of anti ‐2,3‐dibromo‐3‐(4‐chlorosulfonylphenyl)propanoic acid using NaN 3 only was developed. Facile transformation of ( Z )‐4‐(2‐bromovinyl)benzenesulfonyl azide to ( Z )‐ N ‐[4‐ (2‐bromovinyl)benzenesulfonyl]imidates was also achieved by Cu‐catalyzed three‐component coulping of ( Z )‐4‐(2‐bromovinyl)benzenesulfonyl azide, terminal alkynes and alcohols/phenols.