Palladium-catalysed formation of vicinal all-carbon quaternary centres via propargylation

Xin Huang, Shangze Wu, Wangteng Wu, Pengbin Li, Chunling Fu and Shengming Ma ()
Additional contact information
Xin Huang: Laboratory of Molecular Recognition and Synthesis, Zhejiang University
Shangze Wu: Laboratory of Molecular Recognition and Synthesis, Zhejiang University
Wangteng Wu: Laboratory of Molecular Recognition and Synthesis, Zhejiang University
Pengbin Li: Laboratory of Molecular Recognition and Synthesis, Zhejiang University
Chunling Fu: Laboratory of Molecular Recognition and Synthesis, Zhejiang University
Shengming Ma: Laboratory of Molecular Recognition and Synthesis, Zhejiang University

Nature Communications, 2016, vol. 7, issue 1, 1-8

Abstract: Abstract Construction of two vicinal all-carbon quaternary carbon centres is of great importance due to the common presence of such units in natural and unnatural molecules with attractive functions. However, it remains a significant challenge. Here, we have developed a palladium-catalysed general coupling for the efficient connection of two tertiary carbon atoms: Specifically, propargylic carbonate has been treated with a fully loaded soft functionalized nucleophile to connect such two fully loaded carbon atoms with a simple palladium catalyst. It is observed that the central chirality in the optically active tertiary propargylic carbonates has been remembered and transferred into the products with very high efficiency. The triple bond and the functional groups such as ester, cyano and unsaturated C–C bonds make this method a relatively general solution for such a purpose due to their high synthetic versatility.

Date: 2016
References: Add references at CitEc
Citations:

Downloads: (external link)
https://www.nature.com/articles/ncomms12382 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:7:y:2016:i:1:d:10.1038_ncomms12382

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

DOI: 10.1038/ncomms12382

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 ().