Enantioselective Synthesis of (+)-Estrone Exploiting a Hydrogen Bond-Promoted Diels− Alder Reaction

M Weimar, G Dürner, JW Bats…

Index: Weimar, Marko; Duerner, Gerd; Bats, Jan W.; Goebel, Michael W. Journal of Organic Chemistry, 2010 , vol. 75, # 8 p. 2718 - 2721

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Citation Number: 32

Abstract

Starting from Dane's diene and methylcyclopentenedione,(+)-estrone is synthesized along the Quinkert− Dane route in 24% total yield. The key step is an enantioselective Diels− Alder reaction promoted by an amidinium catalyst as efficiently as by a traditional Ti-TADDOLate Lewis acid.

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