A Convenient Synthesis of γ-Amino-Ynamides via Additions of Lithiated Ynamides to Aryl Imines; Observation of an Aza-Meyer–Schuster Rearrangement

Rui Qi; Xiao-Na Wang; Kyle A. DeKorver; Yu Tang; Chao-Chao Wang; Qian Li; Hui Li; Ming-Can Lv; Qing Yu; Richard P. Hsung

doi:10.1055/s-0033-1338476

Synthesis, Inhaltsverzeichnis

Synthesis 2013; 45(13): 1749-1758
DOI: 10.1055/s-0033-1338476

paper

A Convenient Synthesis of γ-Amino-Ynamides via Additions of Lithiated Ynamides to Aryl Imines; Observation of an Aza-Meyer–Schuster Rearrangement

Rui Qi

^aSchool of Pharmaceutical Science and Technology, and Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, Tianjin University, Tianjin 300072, P. R. of China eMail: tangyu114@gmail.com

,

Xiao-Na Wang

^bDepartment of Chemistry and Division of Pharmaceutical Sciences, School of Pharmacy, University of Wisconsin–Madison, Madison, WI 53705, USA eMail: rhsung@wisc.edu

,

Kyle A. DeKorver*

^cDow AgroSciences LLC, 9330 Zionsville Road, Indianapolis, IN 46268, USA Fax: +1(608)2625345 eMail: kadekorver@dow.com

,

Yu Tang*

^aSchool of Pharmaceutical Science and Technology, and Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, Tianjin University, Tianjin 300072, P. R. of China eMail: tangyu114@gmail.com

,

Chao-Chao Wang

^aSchool of Pharmaceutical Science and Technology, and Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, Tianjin University, Tianjin 300072, P. R. of China eMail: tangyu114@gmail.com

,

Qian Li

^aSchool of Pharmaceutical Science and Technology, and Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, Tianjin University, Tianjin 300072, P. R. of China eMail: tangyu114@gmail.com

,

Hui Li

^aSchool of Pharmaceutical Science and Technology, and Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, Tianjin University, Tianjin 300072, P. R. of China eMail: tangyu114@gmail.com

,

Ming-Can Lv

^aSchool of Pharmaceutical Science and Technology, and Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, Tianjin University, Tianjin 300072, P. R. of China eMail: tangyu114@gmail.com

,

Qing Yu

^aSchool of Pharmaceutical Science and Technology, and Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, Tianjin University, Tianjin 300072, P. R. of China eMail: tangyu114@gmail.com

,

Richard P. Hsung*

^bDepartment of Chemistry and Division of Pharmaceutical Sciences, School of Pharmacy, University of Wisconsin–Madison, Madison, WI 53705, USA eMail: rhsung@wisc.edu

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Abstract

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With the deepest respect and admiration, we dedicate this paper to Professor Scott E. Denmark on the very special occasion of his 60^th birthday.

Abstract

Efforts in developing an expeditious and convenient method for synthesizing γ-amino-ynamides via nucleophilic addition of lithiated ynamides to aryl imines are described. This work also features an aza-variant of a Meyer–Schuster rearrangement of γ-amino-ynamides and their synthetic utility in intramolecular ketenimine [2+2] cycloadditions.

Key words

lithiated ynamides - γ-amino-ynamides - aryl imines - azetene - aza-Meyer–Schuster rearrangement

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Referenzen

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24 HRMS (ESI) was attempted, but the sample was not stable enough.