Open AccessHighly enantioselective alkyne additions to aldehydes in the presence of 1,1′-bi-2-naphthol and hexamethylphosphoramide
Author(s) -
Ge Gao,
Ruili Xie,
Lin Pu
Publication year - 2004
Publication title -
proceedings of the national academy of sciences of the united states of america
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.011
H-Index - 771
eISSN - 1091-6490
pISSN - 0027-8424
DOI - 10.1073/pnas.0307136101
Subject(s) - hexamethylphosphoramide , enantioselective synthesis , alkyne , chemistry , reagent , toluene , methylene , chloride , organic chemistry , medicinal chemistry , combinatorial chemistry , catalysis
It is found that the addition of hexamethylphosphoramide to the solution of an alkyne, Et(2)Zn, and (S)-1,1'-bi-2-naphthol in methylene chloride allows the generation of an alkynylzinc at room temperature and shows highly enantioselective additions to aldehydes. The mild condition for the formation of the alkynylzinc reagent enables the use of functional alkynes in this asymmetric reaction with excellent enantioselectivity. It avoids the reflux of the toluene solutions of the alkynes and Et(2)Zn as previously reported.