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  • Enantioselective synthesis of (+)-estrone exploiting a hydrogen bond-promoted Diels-Alder reaction.

Enantioselective synthesis of (+)-estrone exploiting a hydrogen bond-promoted Diels-Alder reaction.

The Journal of organic chemistry (2010-03-23)
Marko Weimar, Gerd Dürner, Jan W Bats, Michael W Göbel
摘要

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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4-Bromo-1-naphthol, 95%