Synthesis of enantioenriched homopropargylic sulfonamides by a three component reaction of aldehydes, sulfonamides, and chiral allenylsilanes.
Enantioenriched allenylsilanes are used as carbon nucleophiles in three-component reactions with in situ generated N-sulfonylimines to selectively form syn-homopropargylic sulfonamides. The reactions proceed with a variety of aldehyde and sulfonamide reaction partners. These novel reaction products are obtained with useful levels of diastereoselectivity, and the axial chirality of the allenylsilane is fully transferred to point chirality, forming products with >97% ee.
Brawn
Ryan A
RA
Department of Chemistry, Metcalf Center for Science and Engineering, 590 Commonwealth Avenue, Boston University, Boston, Massachusetts 02215, USA.
Panek
James S
JS
D000447:Aldehydes / Q000737:chemistry*; D015394:Molecular Structure; D010293:Pargyline / Q000031:analogs & derivatives / Q000737:chemistry*; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism; D013449:Sulfonamides / Q000138:chemical synthesis* / Q000737:chemistry*
D000447:Aldehydes; D012821:Silanes; D013449:Sulfonamides; D010293:Pargyline