Reactions capable of stereoselectively forming all carbon quaternary stereocenters (ACQSs) are of value to the synthetic community. Substrates containing methyl dienol ethers tethered to aliphatic aldehydes undergo a vinylogous aldol reaction (VAR) when exposed to catalytic quantities of toluenesulfonic acid in aqueous tetrahydrofuran to give rise to cyclic aldols containing an ACQS. The paucity of synthetic methods to prepare isomerically pure methyl dienol ethers have hindered the detailed study of this diastereoselective reaction. Described here is the synthesis of isomerically pure VAR substrates with variable tether structures and lengths intended to probe the scope and limitations of the reaction.

Preparation of isomerically pure substrates designed to explore the scope and limitations of an acid-initiated vinylogous aldol reaction

2019 Spring National Meeting

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