Combination of gold and redox enzyme catalysis to access valuable enantioenriched aliphatic β-chlorohydrins

Abstract

The synthesis of enantioenriched β-chlorohydrins is highly appealing due to their relevance as building-blocks in organic synthesis. However, the approximation to aliphatic derivatives is particularly challenging due to the difficulties to get access to the α-chloroketone precursors. Herein, we propose a straightforward and scalable approach combining in a concurrent manner gold(I) and redox enzyme catalysis through a hydration-bioreduction cascade. A total of nine aliphatic β-chlorohydrins bearing different functional groups were obtained with very high yields (63–88%) and stereoselectivities (>99% ee).