Three-component, room temperature crotylation catalyzed by solid-supported Brønsted acid: enantioselective synthesis of homoallylic carbamates.
[reaction: see text] A heterogeneous, three-component crotylation of in situ generated N-acyl iminium ions has been developed. This reaction proceeds under ambient temperature in MeCN and is catalyzed by macroporous polystyrene-bound sulfonic acid (MP-TsOH). Workup is accomplished by filtration, upon which the catalyst is recoverable. A range of homoallylic amine equivalents have been prepared from the corresponding aldehydes, carbamates, and chiral (E)-crotylsilanes in a highly stereoselective manner.
Lipomi
Darren J
DJ
Department of Chemistry and Center for Chemical Methodology and Library Development, Boston University, 590 Commonwealth Avenue, Boston, Massachusetts 02215, USA.
Panek
James S
JS
D002219:Carbamates / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D015394:Molecular Structure; D011137:Polystyrenes / Q000737:chemistry*; D016062:Porosity; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism; D013451:Sulfonic Acids / Q000737:chemistry*; D013696:Temperature
D002219:Carbamates; D011137:Polystyrenes; D012821:Silanes; D013451:Sulfonic Acids; C507609:crotylsilane