Organic Letters 2013-04-19

Diastereoselective synthesis of vicinal tertiary diols.

Brad M Loertscher, Phil R Young, Patrick R Evans, Steven L Castle

Index: Org. Lett. 15(8) , 1930-3, (2013)

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Abstract

A strategy for the synthesis of differentiated vicinal tertiary diols is described. The key step is a high-yielding, diastereoselective LaCl3·2LiCl-mediated addition of a Grignard or organolithium reagent to ketone 2a. The reaction is believed to proceed via a 1,3-chelated intermediate. One of the adducts has been transformed into a functionalized cyclopentenone resembling the core structure of pactamycin.