Successive copper(I)-catalyzed cross-couplings in one pot: a novel and efficient starting point for synthesis of carbapenems.
An efficient approach for synthesizing a series of 2-sulfide carbapenems has been developed using two successive Cu(I)-catalyzed cross-couplings in a single pot. The method involves highly selective intramolecular coupling of lactam and dihaloalkene using 2,2'-bipyridine as a ligand, followed by intermolecular C-S formation in the presence of another ligand (1,10-phenanthroline, PPh 3) and mercaptan.
Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, PRC. jiangb@mail.sioc.ac.cn
Biao
B
Jiang
Hua
H
Tian
Zuo-Gang
ZG
Huang
Min
M
Xu
D000475:Alkenes / Q000737:chemistry; D015780:Carbapenems / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D003432:Cross-Linking Reagents / Q000737:chemistry*; D015394:Molecular Structure; D013455:Sulfur / Q000737:chemistry; D014753:Vinyl Compounds / Q000737:chemistry
D000475:Alkenes; D015780:Carbapenems; D003432:Cross-Linking Reagents; D014753:Vinyl Compounds; D013455:Sulfur; D003300:Copper