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

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• 作者：Marko Weimar ; Gerd Drner ; Jan W. Bats ; Michael W. Gbel
• 刊名：Journal of Organic Chemistry
• 出版年：2010
• 出版时间：April 16, 2010
• 年：2010
• 卷：75
• 期：8
• 页码：2718-2721
• 全文大小：758K
• 年卷期：v.75,no.8(April 16, 2010)
• ISSN：1520-6904

文摘

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.