New approach to the stereoselective synthesis of tertiary methyl ethers.
The Lewis acid-mediated addition of titanium enolates from 1 to dimethyl ketals of aliphatic methyl ketones followed by removal of the chiral auxiliary furnishes enantiomerically pure derivatives containing a tertiary methyl ether and a contiguous stereocenter in a straightforward manner.
Departament de Química Orgànica, Universitat de Barcelona, 08028 Barcelona, Catalonia, Spain.
Begoña
B
Checa
Erik
E
Gálvez
Ricard
R
Parelló
Miriam
M
Sau
Pedro
P
Romea
Fèlix
F
Urpí
Mercè
M
Font-Bardia
Xavier
X
Solans
D002384:Catalysis; D008738:Methyl Ethers / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D014025:Titanium / Q000737:chemistry*
D008738:Methyl Ethers; D014025:Titanium