Diastereoselective synthesis of thieno[3 ',2 ': 4,5]cyclopenta[1,2-d][1,3]-oxazolines - New ligands for the copper-catalyzed asymmetric conjugate addition of diethylzinc to enones

作者：Bonini BF^*; Capito E; Comes Franchini M; Ricci A; Bottoni A; Bernardi F; Miscione GP; Giordano L; Cowley AR

来源：European Journal of Organic Chemistry, 2004, (21): 4442-4451.

DOI：10.1002/ejoc.200400351

• thieno-oxazolines
• conjugate addition
• computational investigation

Several new ligands featuring a rigid three ring skeleton have been prepared for the first time following a modular approach. Chirality has been introduced by use of an oxazoline moiety fused with a cyclopenta[b]thiophene backbone. The efficiency and stereochemical impact of these ligands on the copper-catalyzed enantioselective addition of Et2Zn to chalcone was examined and enantiomeric excesses up to 79% were achieved using the ligand (R,R)-16 substituted with a methyl group at the cyclopenta moiety. Computational and ESI-mass spectral studies show that these new compounds behave as monodentate ligands towards Cu+.

• 出版日期2004-10-25