volume 30 issue 11 pages 1253-1268

2-Azadienes as Enamine Umpolung Synthons for the Preparation of Chiral Amines

Publication typeJournal Article
Publication date2019-03-26
scimago Q3
wos Q3
SJR0.437
CiteScore3.3
Impact factor1.4
ISSN09365214, 14372096
Organic Chemistry
Abstract

The development of new strategies for the preparation of chiral amines is an important objective in organic synthesis. In this Synpacts, we summarize our approach for catalytically accessing nucleophilic aminoalkyl metal species from 2-azadienes, and its application in generating a number of important but elusive chiral amine scaffolds. Reductive couplings with ketones and imines afford 1,2-amino tertiary alcohols and 1,2-diamines, respectively, whereas fluoroarylations of gem-difluoro-2-azadienes deliver α-trifluoromethylated benzylic amines.

1 Introduction

2 Background: Umpolung Strategies for Preparing Chiral Amines

3 Background: 2-Azadienes

4 Reductive Couplings of 2-Azadienes

5 Fluoroarylations of gem-Difluoro-2-azadienes

6 Summary and Outlook

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Malcolmson S. J., Li K., Shao X. 2-Azadienes as Enamine Umpolung Synthons for the Preparation of Chiral Amines // Synlett. 2019. Vol. 30. No. 11. pp. 1253-1268.
GOST all authors (up to 50) Copy
Malcolmson S. J., Li K., Shao X. 2-Azadienes as Enamine Umpolung Synthons for the Preparation of Chiral Amines // Synlett. 2019. Vol. 30. No. 11. pp. 1253-1268.
RIS |
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RIS Copy
TY - JOUR
DO - 10.1055/s-0037-1611770
UR - https://doi.org/10.1055/s-0037-1611770
TI - 2-Azadienes as Enamine Umpolung Synthons for the Preparation of Chiral Amines
T2 - Synlett
AU - Malcolmson, Steven J
AU - Li, Kangnan
AU - Shao, Xinxin
PY - 2019
DA - 2019/03/26
PB - Georg Thieme Verlag KG
SP - 1253-1268
IS - 11
VL - 30
PMID - 33731976
SN - 0936-5214
SN - 1437-2096
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2019_Malcolmson,
author = {Steven J Malcolmson and Kangnan Li and Xinxin Shao},
title = {2-Azadienes as Enamine Umpolung Synthons for the Preparation of Chiral Amines},
journal = {Synlett},
year = {2019},
volume = {30},
publisher = {Georg Thieme Verlag KG},
month = {mar},
url = {https://doi.org/10.1055/s-0037-1611770},
number = {11},
pages = {1253--1268},
doi = {10.1055/s-0037-1611770}
}
MLA
Cite this
MLA Copy
Malcolmson, Steven J., et al. “2-Azadienes as Enamine Umpolung Synthons for the Preparation of Chiral Amines.” Synlett, vol. 30, no. 11, Mar. 2019, pp. 1253-1268. https://doi.org/10.1055/s-0037-1611770.