Chiral Phosphites and Phosphoramidites Based on the Tropane Skeleton and Their Application in Catalysis

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• 作者：Nicolai Cramer ; Sabine Laschat ; and Angelika Baro
• 刊名：Organometallics
• 出版年：2006
• 出版时间：April 24, 2006
• 年：2006
• 卷：25
• 期：9
• 页码：2284 - 2291
• 全文大小：152K
• 年卷期：v.25,no.9(April 24, 2006)
• ISSN：1520-6041

文摘

A class of novel BINOL-containing tropanes was accessible by treating enantiopure (6S)-configuredtropinone acetals 5a and 8 with chlorophosphites 7. When applied to Cu-catalyzed 1,4-additions ofdialkylzinc to cyclic and acyclic enones 14 and 16, the bidentate phosphoramidite (S,S)-9a bearing two(S)-binaphthol units worked selectively in most cases (up to 90% ee). (S,S)-9a was also superior to theother ligands in Rh-mediated hydrogenations of dimethyl itaconate 18 and methyl acetamidocinnamate20 (85% ee and 95% ee). In both reactions, a matched/mismatched case was observed for (S,S)-9a andits congener (R,R)-9a.