Abstract

DBU-catalyzed Michael reactions between tert-butyl 2-((diphenylmethylene) amino)acetate and simple β-substituted α,β-unsaturated esters have been achieved in high yields (up to 95% yield) and diastereoselectivties (up to 99:1 dr) in the presence of 1.0 eq. of LiBr in acetonitrile under room temperature. The Michael adduct can be easily converted into trans-3-substituted pyroglutamic acid ester through in-situ acidic hydrolysis following lactamation.

中文翻译：

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DBU 催化大体积甘氨酸亚胺与 β-芳基呋喃基取代的 α,β-不饱和酯的迈克尔加成反应

摘要

DBU 催化的2-((二苯基亚甲基)氨基)乙酸叔丁酯和简单的 β-取代 α,β-不饱和酯之间的 Michael 反应已实现高产率（高达 95% 的产率）和非对映选择性（高达 99: 1 dr) 在 1.0 eq 存在的情况下 室温下溴化锂在乙腈中的溶液。通过内酰胺化后的原位酸性水解，迈克尔加合物可以很容易地转化为反式-3-取代的焦谷氨酸酯。