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Chiral Ruthenium‐Catalyzed Hydrogenation of β‐Keto Sulfoxides
Author(s) -
Duprat De Paule Sébastien,
Piombo Laurent,
RatovelomananaVidal Virginie,
Greck Christine,
Genêt JeanPierre
Publication year - 2000
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/(sici)1099-0690(200004)2000:8<1535::aid-ejoc1535>3.0.co;2-q
Subject(s) - ruthenium , chemistry , catalysis , noyori asymmetric hydrogenation , chirality (physics) , enantioselective synthesis , organic chemistry , asymmetric hydrogenation , medicinal chemistry , combinatorial chemistry , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark
The diastereoselective catalytic hydrogenation of β‐keto sulfoxides in the presence of ruthenium complexes was studied. Optically pure β‐keto sulfoxides were hydrogenated in the presence of achiral catalysts leading to moderate yields and stereoselectivities. Using chiral ruthenium catalysts such as [( R )‐MeO‐BIPHEPRuBr 2 ] and [( S )‐MeO‐BIPHEPRuBr 2 ], the hydrogenation proceeded in good yields with very high diastereoselectivity. Chirality at the secondary centre of the β‐hydroxy sulfoxides produced was controlled by the catalysts.