Reductive olefination of aldehydes via chromium Brook rearrangement.
[reaction: see text] The combination of CrCl(2) and silyl chlorides converts aryl and conjugated aldehydes into olefinic adducts in good to excellent yields. When constrained by structural features, the intermediate vic-diol can be isolated. Available data are consistent with a novel chromium Brook rearrangement.
Baati
Rachid
R
Laboratoire de Synthèse Bio-Organique, UMR 7175/LC1-CNRS, Faculté de Pharmacie, Université Louis Pasteur de Strasbourg, Illkirch, France.
Mioskowski
Charles
C
Barma
Deb
D
Kache
Rajashaker
R
Falck
J R
JR
D000447:Aldehydes / Q000737:chemistry*; D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D002857:Chromium / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D012821:Silanes / Q000737:chemistry*
D000447:Aldehydes; D000475:Alkenes; D009942:Organometallic Compounds; D012821:Silanes; D002857:Chromium