Thiol-free chemoenzymatic synthesis of β-ketosulfides

• Adrián A. Heredia,
• Martín G. López-Vidal,
• Marcela Kurina-Sanz,
• Fabricio R. Bisogno and
• Alicia B. Peñéñory

Beilstein J. Org. Chem. 2019, 15, 378–387, doi:10.3762/bjoc.15.34

• Orgánica, Facultad de Química, Bioquímica y Farmacia, UNSL. Chacabuco y Pedernera, San Luis, 5700, Argentina 10.3762/bjoc.15.34 Abstract A preparation of β-ketosulfides avoiding the use of thiols is described. The combination of a multicomponent reaction and a lipase-catalysed hydrolysis has been

• developed in order to obtain high chemical diversity employing a single sulfur donor. This methodology for the selective synthesis of a set of β-ketosulfides is performed under mild conditions and can be set up in one-pot two-step and on a gram-scale. Keywords: ketosulfides; lipase; multicomponent

• thiols (Scheme 1) [17][18][19][20][21], other methodologies employing different sulfur sources such as disulfides or silylsulfides have been described, which most of them involves metals, e.g., indium [22], copper [23], mercury [24], or organocatalysts [25]. β-Ketosulfides, in addition, play an important