Design of Structurally Rigid trans-Diamine-Based Tf-Amide Organocatalysts with a Dihydroanthracene Framework for Asymmetric Conjugate Additions of Heterosubstituted Aldehydes to Vinyl Sulfones

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• 作者：Shin A. Moteki ; Senmiao Xu ; Satoru Arimitsu ; Keiji Maruoka
• 刊名：Journal of the American Chemical Society
• 出版年：2010
• 出版时间：December 8, 2010
• 年：2010
• 卷：132
• 期：48
• 页码：17074-17076
• 全文大小：164K
• 年卷期：v.132,no.48(December 8, 2010)
• ISSN：1520-5126

文摘

Asymmetric conjugate addition of α-heterosubstituted aldehydes such as α-amido and α-alkoxy aldehydes to vinyl sulfone was effected under the influence of structurally rigid trans-diamine-based Tf-amido organocatalyst (S,S)-2 with a dihydroanthracene framework to furnish α,α-dialkyl(amido)aldehydes and α,α-dialkyl(alkoxy)aldehydes with high enantioselectivity. The chiral efficiency of the structurally unique catalyst (S,S)-2 is apparent in comparison with (S,S)-1 and (S,S)-4 with similar functionality.