A novel pyridyl sulfone addition/elimination sequence has been discovered that leads to the stereoselective construction of pyridine-containing allylic alcohol products. Mechanistic investigations with the 2-substituted pyridyl sulfone suggest that the reaction proceeds via a picolyl/sulfonyl dianion generated with n-butyllithium. This dianion then reacts regioselectively with various aldehydes followed by elimination of the sulfone group to give exclusively trans-coupled products. Preliminary studies with a 4-substituted pyridyl sulfone demonstrate that this reaction is not limited only to the 2-series and may be amenable to a variety of heterocyclic substrates.

Addition/elimination reactions of pyridyl sulfones

245th National Meeting (2013)

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