Regioselective allene synthesis and propargylations with propargyl diethanolamine boronates.
The utility of propargyl diethanolamine boronates as reagents for the preparation of allenes and homopropargylic alcohols is presented. Protonolysis with TFA and electrophilic substitution with N-halosuccinimides proceeded with inversion to provide the corresponding allene in high yield and regioselectivity. Alternatively, the propargylation of aldehydes was achieved with use of the in situ generated lithiated complex.
Fandrick
Daniel R
DR
Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals Inc., 900 Old Ridgebury Road, P.O. Box 368, Ridgefield, Connecticut 06877-0368, USA. daniel.fandrick@boehringer-ingelheim.com
Reeves
Jonathan T
JT
Tan
Zhulin
Z
Lee
Heewon
H
Song
Jinhua J
JJ
Yee
Nathan K
NK
Senanayake
Chris H
CH
D000466:Alkadienes / Q000138:chemical synthesis* / Q000737:chemistry; D001896:Boron Compounds / Q000737:chemistry*; D002384:Catalysis; D004983:Ethanolamines / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D000466:Alkadienes; D001896:Boron Compounds; D004983:Ethanolamines; C025947:propadiene; C020283:diethanolamine