Tuning efficiency of the 4-exo-trig cyclization by the electronic effect: ring closure of 3,3-difluoro-4-pentenyl carbon radicals and synthesis of a gem-difluorocyclobutane nucleoside | Zendy

Hiroki Kumamoto | Zendy; Sachiko Kawahigashi | Zendy; Hiromi Wakabayashi | Zendy; Tomohiko Nakano | Zendy; Tomoko Miyaike | Zendy; Yasuyuki Kitagawa | Zendy; Hiroshi Abe | Zendy; Mika Ito | Zendy; Kazuhiro Haraguchi | Zendy; Jan Balzarini | Zendy; Masanori Baba | Zendy; Hiromichi Tanaka | Zendy

Open Access

Tuning efficiency of the 4-exo-trig cyclization by the electronic effect: ring closure of 3,3-difluoro-4-pentenyl carbon radicals and synthesis of a gem-difluorocyclobutane nucleoside

Author(s) -

Hiroki Kumamoto,

Sachiko Kawahigashi,

Hiromi Wakabayashi,

Tomohiko Nakano,

Tomoko Miyaike,

Yasuyuki Kitagawa,

Hiroshi Abe,

Mika Ito,

Kazuhiro Haraguchi,

Jan Balzarini,

Masanori Baba,

Hiromichi Tanaka

Publication year - 2012

Publication title -

chemical communications

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.837

H-Index - 333

eISSN - 1364-548X

pISSN - 1359-7345

DOI - 10.1039/c2cc35876j

Subject(s) - moiety , chemistry , radical , radical cyclization , ring (chemistry) , derivative (finance) , nucleoside , carbon fibers , closure (psychology) , medicinal chemistry , stereochemistry , combinatorial chemistry , organic chemistry , materials science , financial economics , economics , market economy , composite number , composite material

4-exo-trig Cyclization reaction of a 4-pentenyl carbon radical containing the gem-difluoromethylene moiety adjacent to a radical accepting α,β-unsaturated ester was found to proceed efficiently to furnish a novel gem-difluorocyclobutane derivative. The cyclized product could be transformed into a gem-difluoromethylene analogue of oxetanocin T.

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