Aminocatalytic Synthesis of Uracil Derivatives Bearing a Bicyclo[2.2.2]octane Scaffold via a Doubly Cycloadditive Reaction Cascade,Synthesis

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Aminocatalytic Synthesis of Uracil Derivatives Bearing a Bicyclo[2.2.2]octane Scaffold via a Doubly Cycloadditive Reaction Cascade
Synthesis ( IF 2.6 ) Pub Date : 2020-10-22 , DOI: 10.1055/s-0040-1707313
Łukasz Albrecht , Maciej Saktura , Sebastian Frankowski , Bartłomiej Joachim

Dedicated to Professor Grzegorz Mlostoń on the occasion of his 70^th birthday

Abstract

Aminocatalytic synthesis of highly enantiomerically enriched uracil derivatives bearing a bicyclo[2.2.2]octane scaffold is described. The developed strategy utilizes 1,3,6-trimethyl-5-formyluracil and α,β-unsaturated aldehydes as starting materials and has been realized employing various aminocatalytic activation strategies operating in a synergistic manner. The reaction cascade can be described as doubly cycloadditive as it consists of two consecutive Diels–Alder cycloadditions allowing for a facile construction of the bicyclo[2.2.2]octane scaffold. Notably, both steps proceed with dearomatization of the partially aromatic uracil moiety. Excellent stereoselectivity of the reaction cascade is ensured by the use of 2-(diphenylmethyl)pyrrolidine as aminocatalyst.

Publication History

Received: 06 August 2020

Accepted after revision: 02 September 2020

Publication Date:
22 October 2020 (online)

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

中文翻译：

经由双环加成反应级联的氨基催化合成双环[2.2.2]辛烷骨架的尿嘧啶衍生物

专用于格热戈日Mlostoń教授在他的70之际^个生日

抽象

描述了带有双环[2.2.2]辛烷骨架的高度对映体富集的尿嘧啶衍生物的氨基催化合成。所开发的策略利用1,3,6-三甲基-5-甲酰基尿嘧啶和α，β-不饱和醛作为起始原料，并已通过采用各种以协同方式起作用的氨基催化活化策略来实现。反应级联可以描述为双环加成，因为它由两个连续的Diels-Alder环加成组成，可轻松构建双环[2.2.2]辛烷骨架。值得注意的是，两个步骤均进行部分芳族尿嘧啶部分的脱芳香化。通过使用2-（二苯甲基）吡咯烷作为氨基催化剂，可以确保反应级联的出色立体选择性。