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  • Enantioselective synthesis of substituted piperidines by addition of aryl Grignard reagents to pyridine N-oxides.

Enantioselective synthesis of substituted piperidines by addition of aryl Grignard reagents to pyridine N-oxides.

Organic letters (2012-12-22)
Munawar Hussain, Thomas Sainte-Luce Banchelin, Hans Andersson, Roger Olsson, Fredrik Almqvist
ABSTRACT

The synthesis of optically active piperidines by enantioselective addition of aryl Grignard reagents to pyridine N-oxides and lithium binolate followed by reduction is reported for the first time. The reaction results in high yields (51-94%) in combination with good ee (54-80%). Some of these products were subsequently recrystallized, affording enhanced optical purities (>99% ee).

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Pyridine N-oxide, 95%