Triflimide (HNTf2)-catalyzed aldehyde cross-aldol reaction using "super silyl" enol ethers.
The synthesis of the acetaldehyde-derived tris(trimethylsilyl)silyl (super silyl) enol ether is described, as well as its use in the high-yielding aldehyde cross-aldol reaction. The super silyl enol ether shows unprecedented reactivity in giving the 1:1 adduct in very high yield. This reaction is catalyzed by 0.05 mol% of the Brønsted acid triflimide (HNTf2) and is complete within 15 min, making the protocol very attractive for large-scale synthesis.
Boxer
Matthew B
MB
Department of Chemistry, The University of Chicago, 5735 South Ellis Avenue, Chicago, Illinois 60637, USA.
Yamamoto
Hisashi
H
D000447:Aldehydes / Q000737:chemistry*; D003512:Cyclohexanones / Q000737:chemistry; D014297:Trimethylsilyl Compounds / Q000138:chemical synthesis / Q000737:chemistry*
D000447:Aldehydes; D003512:Cyclohexanones; D014297:Trimethylsilyl Compounds; C518058:triflimide; C523681:tris(trimethylsilyl)silyl enol ether