Catalytic asymmetric total syntheses of quinine and quinidine

…, SN Goodman, EN Jacobsen

文献索引：Raheem, Izzat T.; Goodman, Steven N.; Jacobsen, Eric N. Journal of the American Chemical Society, 2004 , vol. 126, # 3 p. 706 - 707

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被引用次数: 149

摘要

The catalytic, asymmetric syntheses of quinine and quinidine were achieved in 16 steps. The recently developed salen (Al)-catalyzed enantioselective Michael addition of methyl cyanoacetate served to set the crucial C4 stereocenter in 92% ee, and a late-stage asymmetric dihydroxylation was used to differentiate the common intermediate and access the two desired diastereomeric products with high selectivity.