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Readily Available Ruthenium Complex for Efficient Dynamic Kinetic Resolution of Aromatic α-Hydroxy Ketones
Author(s) -
Santosh Agrawal,
Elisa MartínezCastro,
Rocı́o Marcos,
Belén MartínMatute
Publication year - 2014
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/ol500764q
Subject(s) - racemization , kinetic resolution , chemistry , ruthenium , pseudomonas stutzeri , lipase , catalysis , butane , kinetic energy , resolution (logic) , organic chemistry , enantioselective synthesis , enzyme , physics , quantum mechanics , artificial intelligence , biology , bacteria , computer science , genetics
A ruthenium complex formed from commercially available [Ru(p-cymene)Cl2]2 and 1,4-bis(diphenylphosphino)butane catalyzes the racemization of aromatic α-hydroxy ketones very efficiently at room temperature. The racemization is fully compatible with a kinetic resolution catalyzed by a lipase from Pseudomonas stutzeri. This is the first example of dynamic kinetic resolution of α-hydroxy ketones at ambient temperature in which the metal and enzyme catalysts work in concert in one pot at room temperature to give quantitative yields of esters of α-hydroxy ketones with very high enantioselectivity.

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