Abstract

Asymmetric intramolecular Michael-aldol reaction of (−)-phenylmenthyl enoates 1 affords tricyclic cyclobutanes 2 in excellent diastereoselectivity. It is made clear that Michael-aldol reaction is reversible under conditions using trimethylsilyl iodide (TMSI) in the presence of hexamethyldisilazane (HMDS) at ambient temperature. The difference of stereoselectivity under kinetic or thermodynamic conditions are reported.

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