Hydrostannylation–Cross‐Coupling Strategy for the Stereoselective Synthesis of Alkylidenemalonates and Related α,β‐Unsaturated Esters | Zendy

Fujiwara Shinichi | Zendy; Cadou Romain | Zendy; Yamaoka Yousuke | Zendy; Takasu Kiyosei | Zendy; Yamada Kenichi | Zendy

Premium

Hydrostannylation–Cross‐Coupling Strategy for the Stereoselective Synthesis of Alkylidenemalonates and Related α,β‐Unsaturated Esters

Author(s) -

Fujiwara Shinichi,

Cadou Romain,

Yamaoka Yousuke,

Takasu Kiyosei,

Yamada Kenichi

Publication year - 2015

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.201403429

Subject(s) - stille reaction , chemistry , stereoselectivity , coupling (piping) , coupling reaction , catalysis , combinatorial chemistry , organic chemistry , engineering , mechanical engineering

A method for the stereoselective synthesis of alkylidenemalonates and related α,β‐unsaturated esters by a hydrostannylation–cross‐coupling process has been developed. Pd‐catalyzed and radical hydrostannylation of propiolate derivatives stereoselectively provided α‐alkoxycarbonyl ( E )‐ and ( Z )‐vinylstannanes, respectively, which were then converted into alkylidenemalonates by the Stille coupling reaction. A one‐pot process was also realizable for the Pd‐catalyzed reactions.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research