Organozinc reagents in DMSO solvent: remarkable promotion of SN2' reaction for allene synthesis.
The S N2' reaction of propragyl mesylates with organozinc reagents was dramatically improved in DMSO solvent, and the stereoselective conversion of chiral substrates was successfully achieved using LiCl-free diorganozinc without the loss of optical purity.
Kobayashi
Koji
K
Graduate School of Pharmaceutical Sciences, Tohoku University, Aramaki-aza Aoba 6-3, Aoba-ku, Sendai 980-8578, Japan.
Naka
Hiroshi
H
Wheatley
Andrew E H
AE
Kondo
Yoshinori
Y
D000466:Alkadienes / Q000138:chemical synthesis*; D000480:Alkynes / Q000737:chemistry*; D004121:Dimethyl Sulfoxide / Q000737:chemistry; D008698:Mesylates / Q000737:chemistry; D009942:Organometallic Compounds / Q000737:chemistry*; D015032:Zinc / Q000737:chemistry*
D000466:Alkadienes; D000480:Alkynes; D008698:Mesylates; D009942:Organometallic Compounds; C025947:propadiene; D015032:Zinc; D004121:Dimethyl Sulfoxide