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Synthesis of Novel Bis(β‐lactam)‐1,3‐diynes by Copper‐Promoted Homo‐ or Cross‐Coupling of Alkynyl‐2‐azetidinones
Author(s) -
Alcaide Benito,
Almendros Pedro,
Carrascosa Rocío,
RodríguezAcebes Raquel
Publication year - 2008
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.200701083
Subject(s) - chemistry , lactam , enantiopure drug , amine gas treating , copper , stereochemistry , combinatorial chemistry , medicinal chemistry , enantioselective synthesis , catalysis , organic chemistry
Abstract Cu(OAc) 2 in combination with K 2 CO 3 (a solid base instead of an amine) was proven to be an extremely effective system for promoting the homocoupling of various (β‐lactam)acetylenes to afford C 2 ‐symmetrical bis(β‐lactam)‐1,3‐diynes, whereas these 2‐azetidinone‐tethered alkynes underwent the Cadiot–Chodkiewicz cross‐coupling reaction with different 2‐azetidinone bromoalkynes to form a variety of unsymmetrical bis(β‐lactam)diynes in good yields. In addition to their potential biological activity, the resulting enantiopure bis(β‐lactam)‐1,3‐diynes can be converted into bis(β‐amino ester)‐1,3‐diynes, which may find use as macrocyclic cavities, as well as chiral ligands. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)