A chiral Brønsted acid-catalyzed highly enantioselective Mannich-type reaction of α-diazo esters with in situ generated N-acyl ketimines†‡,Chemical Communications

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A chiral Brønsted acid-catalyzed highly enantioselective Mannich-type reaction of α-diazo esters with in situ generated N-acyl ketimines†‡
Chemical Communications ( IF 4.3 ) Pub Date : 2018-03-14 00:00:00 , DOI: 10.1039/c8cc01436a
Rajshekhar A. Unhale _{1,

2,

3,

4} , Milon M. Sadhu _{1,

2,

3,

4} , Sumit K. Ray _{1,

2,

3,

4} , Rayhan G. Biswas _{1,

2,

3,

4} , Vinod K. Singh _{1,

1,

2,

3,

4}

Affiliation

A chiral phosphoric acid-catalyzed asymmetric Mannich-type reaction of α-diazo esters with in situ generated N-acyl ketimines, derived from 3-hydroxyisoindolinones has been demonstrated in this communication. A variety of isoindolinone-based α-amino diazo esters bearing a quaternary stereogenic center were afforded in high yields (up to 99%) with excellent enantioselectivities (up to 99% ee). Furthermore, the synthetic utility of the products has been depicted by the hydrogenation of the diazo moiety of adducts.

中文翻译：

手性布朗斯台德酸催化α-重氮酯与原位生成的N-酰基酮亚胺的高对映选择性曼尼希型反应† ‡

在该文献中已经证明了手性磷酸催化α-重氮酯与原位生成的由3-羟基异吲哚满酮衍生的N-酰基酮亚胺的不对称曼尼希型反应。以高收率（高达99％）和优异的对映选择性（高达99％ee）提供了多种带有季立构中心的基于异吲哚啉酮的α-氨基重氮酯。此外，通过加合物的重氮部分的氢化描述了产物的合成效用。

更新日期：2018-03-14

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