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Stereodefined Construction of Trisubstituted Alkenes by Direct Coupling Reaction of Allylating Agents, Alkynes, and Organoboranes
Author(s) -
Fukushima Masahiro,
Takushima Daiki,
Satomura Hideaki,
Onodera Gen,
Kimura Masanari
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201201138
Subject(s) - geminal , alkyne , chemistry , allylic rearrangement , acetylene , alkene , alkyl , combinatorial chemistry , medicinal chemistry , organic chemistry , catalysis
Tandem reaction : The Pd‐catalyzed three‐component coupling reaction of an allylic alcohol, terminal alkyne, and organoborane to give ( E )‐1‐substituted 2‐alkyl‐1,4‐pentadienes, involving geminal allylation and alkylation at the acetylenic terminal carbon, is described. Bis‐diene undergoes a similar multicomponent coupling reaction with acetylene and organoborane, involving cyclization of bis‐π‐allylpalladium, to form trans ‐allyl pentadienyl cyclic and heterocyclic compounds with excellent regio‐ and stereoselectivities (see scheme).