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通过有机催化α-氰基乙酸酯与甲基丙烯酸酯类似物的共轭加成实现全碳叔/季非相邻立体中心的不对称组装。

Asymmetric Assembly of All-Carbon Tertiary/Quaternary Nonadjacent Stereocenters through Organocatalytic Conjugate Addition of α-Cyanoacetates to a Methacrylate Equivalent.

作者信息

Iriarte Igor, Vera Silvia, Badiola Eider, Mielgo Antonia, Oiarbide Mikel, García Jesús M, Odriozola José M, Palomo Claudio

机构信息

Departamento de Química Orgánica I, Universidad del País Vasco UPV/EHU, Manuel Lardizabal 3, 20018, San Sebastián, Spain.

Departamento de Química Aplicada, Universidad Pública de Navarra, 31006, Pamplona, Spain.

出版信息

Chemistry. 2016 Sep 12;22(38):13690-6. doi: 10.1002/chem.201603082. Epub 2016 Aug 3.

DOI:10.1002/chem.201603082
PMID:27487331
Abstract

An efficient, highly diastereo- and enantioselective assembly of acyclic carbonyl fragments possessing nonadjacent all-carbon tertiary/quaternary stereoarrays is reported based on a Brønsted base catalyzed Michael addition/α-protonation sequence involving α-cyanoacetates and 2,4-dimethyl-4-hydroxypenten-3-one as novel methacrylate equivalent.

摘要

报道了一种基于布朗斯特碱催化的迈克尔加成/α-质子化序列，以α-氰基乙酸酯和2,4-二甲基-4-羟基戊-3-酮作为新型甲基丙烯酸酯等价物，高效、高非对映选择性和对映选择性地构建具有非相邻全碳叔/季立体阵列的无环羰基片段的方法。

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