Asymmetric Conjugate Reduction of α,β-Unsaturated Ketones and Esters with Chiral Rhodium(2,6-bisoxazolinylphenyl) Catalysts

Autor:	Takushi Shiomi, Jun-ichi Itoh, Yasunori Tsuchiya, Yoshihiko Yamamoto, Yoshinori Kanazawa, Kazuki Kobayashi, Hisao Nishiyama, Makoto Kikuchi
Rok vydání:	2006
Předmět:	Hydrogen Chemistry Organic Chemistry Enantioselective synthesis Organic chemistry chemistry.chemical_element General Medicine General Chemistry Medicinal chemistry Catalysis Conjugate Rhodium
Zdroj:	Chemistry - A European Journal. 12:63-71
ISSN:	1521-3765 0947-6539
DOI:	10.1002/chem.200500841
Popis:	New asymmetric conjugate reduction of beta,beta-disubstituted alpha,beta-unsaturated ketones and esters was accomplished with alkoxylhydrosilanes in the presence of chiral rhodium(2,6-bisoxazolinylphenyl) complexes in high yields and high enantioselectivity. (E)-4-Phenyl-3-penten-2-one and (E)-4-phenyl-4-isopropyl-3-penten-2-one were readily reduced at 60 degrees C in 95 % ee and 98 % ee, respectively, by 1 mol % of catalyst loading. (EtO)2MeSiH proved to be the best hydrogen donor of choice. tert-Butyl (E)-beta-methylcinnamate and beta-isopropylcinnamate could also be reduced to the corresponding dihydrocinnamate derivatives up to 98 % ee.
Databáze:	OpenAIRE
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