Premium
Asymmetric Addition of Propargylic Silanes to Aldehydes Catalyzed by Chiral Phosphine‐Silver Alkoxide Complex
Author(s) -
Yanagisawa Akira,
Bamba Kentaro,
Kawada Aiko
Publication year - 2018
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201802999
Subject(s) - silanes , catalysis , phosphine , triethylamine , chemistry , alkoxide , organic chemistry , hydrosilylation , enantioselective synthesis , methanol , medicinal chemistry , silane
A catalytic asymmetric addition of propargylic silanes to aldehydes was achieved using a DM‐BINAP⋅AgBF 4 complex as the chiral pre‐catalyst and triethylamine as the base pre‐catalyst in the presence of potassium fluoride and methanol. Optically active homoallenylic alcohols and homopropargylic alcohols were obtained in moderate to high combined yields via the in situ generated chiral organosilver species. Allenylated alcohols were formed predominantly with up to 95% ee.