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

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 cop...

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Bibliographic Details
Published in:European journal of organic chemistry 2004-11, Vol.2004 (21), p.4442-4451
Main Authors: Bonini, Bianca Flavia, Capitò, Elena, Comes-Franchini, Mauro, Ricci, Alfredo, Bottoni, Andrea, Bernardi, Fernando, Miscione, Gian Pietro, Giordano, Laurent, Cowley, Andrew R.
Format: Article
Language:English
Subjects:
Computational investigation
Conjugate addition
Thieno-oxazolines
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Summary: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+. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200400351