Isothiourea-mediated stereoselective C-acylation of silyl ketene acetals.
Isothiourea DHPB promotes the diastereoselective C-acylation of silyl ketene acetals with anhydrides or benzoyl fluoride, giving 3-acyl-3-aryl or 3-acyl-3-alkylfuranones in excellent yields and stereoselectivities (up to 99:1 dr).
Woods
Philip A
PA
EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, St. Andrews KY16 9ST, UK.
Morrill
Louis C
LC
Lebl
Tomas
T
Slawin
Alexandra M Z
AM
Bragg
Ryan A
RA
Smith
Andrew D
AD
D000080:Acetals / Q000737:chemistry*; D000215:Acylation; D000812:Anhydrides / Q000737:chemistry; D002384:Catalysis; D005030:Ethylenes / Q000737:chemistry*; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism; D013890:Thiourea / Q000737:chemistry*
D000080:Acetals; D000812:Anhydrides; D005030:Ethylenes; D005663:Furans; D007659:Ketones; D012821:Silanes; D013890:Thiourea; C008223:ketene