Ni(II)-catalyzed asymmetric alkenylations of ketimines

Mao Quan, Xiaoxiao Wang, Liang Wu, Ilya D. Gridnev, Guoqiang Yang () and Wanbin Zhang ()
Additional contact information
Mao Quan: School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University
Xiaoxiao Wang: School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University
Liang Wu: School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University
Ilya D. Gridnev: Graduate School of Science, Tohoku University
Guoqiang Yang: School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University
Wanbin Zhang: School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University

Nature Communications, 2018, vol. 9, issue 1, 1-11

Abstract: Abstract Chiral allylic amines are not only present in many bioactive compounds, but can also be readily transformed to other chiral amines. Therefore, the asymmetric synthesis of chiral allylic amines is highly desired. Herein, we report two types of Ni(II)-catalyzed asymmetric alkenylation of cyclic ketimines for the preparation of chiral allylic amines. When ketimines bear alkyl or alkoxycarbonyl groups, the alkenylation gives five- and six-membered cyclic α-tertiary allylic amine products with excellent yields and enantioselectivities under mild reaction conditions. A variety of ketimines can be used and the method tolerates some variation in alkenylboronic acid scope. Furthermore, with alkenyl five-membered ketimine substrates, an alkenylation/rearrangement reaction occurs, providing seven-membered chiral sulfamide products bearing a conjugated diene skeleton with excellent yields and enantioselectivities. Mechanistic studies reveal that the ring expansion step is a stereospecific site-selective process, which can be catalyzed by acid (Lewis acid or Brønsted acid).

Date: 2018
References: Add references at CitEc
Citations:

Downloads: (external link)
https://www.nature.com/articles/s41467-018-04645-3 Abstract (text/html)

Related works:
This item may be available elsewhere in EconPapers: Search for items with the same title.

Export reference: BibTeX RIS (EndNote, ProCite, RefMan) HTML/Text

Persistent link: https://EconPapers.repec.org/RePEc:nat:natcom:v:9:y:2018:i:1:d:10.1038_s41467-018-04645-3

Ordering information: This journal article can be ordered from
https://www.nature.com/ncomms/

DOI: 10.1038/s41467-018-04645-3

Access Statistics for this article

Nature Communications is currently edited by Nathalie Le Bot, Enda Bergin and Fiona Gillespie

More articles in Nature Communications from Nature
Bibliographic data for series maintained by Sonal Shukla () and Springer Nature Abstracting and Indexing ().