Diastereoselective synthesis of vicinal tertiary diols
Brad M Loertscher1, Phil R Young, Patrick R Evans
1Department of Chemistry and Biochemistry, Brigham Young University, Provo, Utah 84602, United States.
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.
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