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Synthesis of anti ‐1,3‐Diols through RuCl 3 /PPh 3 ‐Mediated Hydrogenation of β‐Hydroxy Ketones: An Alternative to Organoboron Reagents
Author(s) -
Roche Christophe,
Labeeuw Olivier,
Haddad Mansour,
Ayad Tahar,
Genet JeanPierre,
RatovelomananaVidal Virginie,
Phansavath Phannarath
Publication year - 2009
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.200900316
Subject(s) - chemistry , reagent , catalysis , organic chemistry , organoboron compounds , noyori asymmetric hydrogenation , hydrogen , ketone , combinatorial chemistry , enantioselective synthesis
Hydrogenation of enantioenriched β‐hydroxy ketones promoted by the catalyst generated in situ from commercially available and inexpensive RuCl 3 and PPh 3 under hydrogen pressure allowed the efficient preparation of a variety of anti ‐1,3‐diols in good yields and with a high level of diastereoselectivity. This method should be an interesting alternative to organoboron reagents for the diastereoselective reduction of β‐hydroxy ketones. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)