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A Practical Synthesis of Valuable Strained Eight‐Membered‐Ring Derivatives for Click Chemistry
Author(s) -
Bernard Sabrina,
Kumar Ramar Arun,
Porte Karine,
Thuéry Pierre,
Taran Frédéric,
Audisio Davide
Publication year - 2018
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.201800139
Subject(s) - chemistry , click chemistry , cyclopropanation , cyclooctene , ring (chemistry) , combinatorial chemistry , catalysis , stereochemistry , organic chemistry
A convenient and cost‐effective synthetic access to cyclooctyne and trans ‐cyclooctene derivatives is described. A cyclopropanation step using copper powder in place of Rh 2 (OAc) 4 as catalyst and a symmetric diazomalonate resulted in a drastic decrease in the overall cost of the synthesis. Further derivatizations allowed us to characterize, for the first time, the structure of a BCN analogue by X‐ray crystallography, and to obtain a library of derivatives that could potentially be useful for applications in metal‐free click chemistry.