Download PDF
Synlett 2020; 31(16): 1543-1550
DOI: 10.1055/s-0040-1707157
synpacts
© Georg Thieme Verlag Stuttgart · New York

Decarboxylative Umpolung Synthesis of Amines from Carbonyl Compounds

Wen-Wen Chen
,
Baoguo Zhao  ∗
The Education Ministry Key Lab of Resource Chemistry and Shanghai Key Laboratory of Rare Earth Functional Materials and College of Chemistry and Materials Science, Shanghai Normal University, 100 Guilin Road, Shanghai 200234, P. R. of China   Email: zhaobg2006@shnu.edu.cn
› Author AffiliationsWe are grateful for the generous financial support from the National Natural Science Foundation of China (Grant No. 21672148 and 21871181), the Shanghai Municipal Education Commission (Grant No. 2019-01-07-00-02-E00029), the Science and Technology Commission of Shanghai Municipality (Grant No.19XD1402700), and the Shanghai Engineering Research Center of Green Energy Chemical Engineering.
Further Information

Publication History

Received: 14 May 2020

Accepted after revision: 23 May 2020

Publication Date:
12 July 2020 (online)

    Permissions and Reprints All articles of this category


Abstract

2-Azaallyl anions are valuable intermediates which have versatile applications in functionalization with various electrophiles. Decarboxylation of the imines formed from aromatic aldehydes and α,α-diphenylglycine provides an interesting and efficient way to generate delocalized 2-azaallyl anions, which display high reactivity toward different electrophiles with excellent regioselectivity at the diphenylketimino aryl carbon of the 2-azaallyl anions. The transformation produces various amines in good yields under very mild conditions. This Synpacts article highlights the recent advances on the decarboxylative umpolung synthesis of amines from carbonyl compounds.

1 Introduction

2 Decarboxylative Umpolung Reactions of Carbonyl Compounds with Different Electrophiles

2.1 Reaction with π-Allyl–Pd(II) Species

2.2 Reaction with Morita–Baylis–Hillman Adducts

2.3 Reaction with Imines

2.3.1 Intermolecular Reaction with N-Ts Imines

2.3.2 Intramolecular Reaction with Chiral N-tert-Butanesulfinyl Imines

2.4 Reaction with Aldehydes and Ketones

3 Decarboxylative Umpolung Reaction of α,β-Unsaturated Aldehydes with Aldehydes

4 Conclusion

Key words

aminative umpolung - decarboxylative umpolung - decarboxylative coupling - decarboxylation - 2-azaallyl anion - α-amino carbanion