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Copper‐Catalyzed γ‐Selective and Stereospecific Allylic Cross‐Coupling with Secondary Alkylboranes
Author(s) -
Yasuda Yuto,
Nagao Kazunori,
Shido Yoshinori,
Mori Seiji,
Ohmiya Hirohisa,
Sawamura Masaya
Publication year - 2015
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.201501055
Subject(s) - allylic rearrangement , stereospecificity , stereoselectivity , stereocenter , copper , triphenylphosphine , chemistry , catalysis , selectivity , combinatorial chemistry , ligand (biochemistry) , coupling reaction , medicinal chemistry , stereochemistry , organic chemistry , enantioselective synthesis , biochemistry , receptor
The scope of the copper‐catalyzed coupling reactions between organoboron compounds and allylic phosphates is expanded significantly by employing triphenylphosphine as a ligand for copper, allowing the use of secondary alkylboron compounds. The reaction proceeds with complete γ‐ E ‐selectivity and preferential 1,3‐ syn stereoselectivity. The reaction of γ‐silicon‐substituted allylic phosphates affords enantioenriched α‐stereogenic allylsilanes.