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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
Author(s) -
Bonini Bianca Flavia,
Capitò Elena,
ComesFranchini Mauro,
Ricci Alfredo,
Bottoni Andrea,
Bernardi Fernando,
Miscione Gian Pietro,
Giordano Laurent,
Cowley Andrew R.
Publication year - 2004
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.200400351
Subject(s) - chemistry , diethylzinc , moiety , oxazoline , enantioselective synthesis , stereochemistry , denticity , axial chirality , chalcone , thiophene , enantiomer , conjugate , chirality (physics) , ligand (biochemistry) , combinatorial chemistry , medicinal chemistry , catalysis , organic chemistry , crystal structure , mathematical analysis , biochemistry , nambu–jona lasinio model , mathematics , chiral symmetry breaking , physics , receptor , quantum mechanics , quark
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 Et 2 Zn 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)