Stereocontrolled synthesis of spirooxindoles through Lewis acid-promoted [5 + 2]-annulation of chiral silyl alcohols.
The enantioselective synthesis of stereochemically and structurally diverse spirocyclic oxindoles by [5 + 2]-annulation of chiral crotylsilanes bearing a primary alcohol is described. The annulation products were further elaborated to polycyclic oxindoles by Pd(0) catalysis.
Zhang
Yun
Y
Department of Chemistry, Metcalf Center for Science and Engineering, Boston University, 590 Commonwealth Avenue, Boston, Massachusetts 02215, USA.
Panek
James S
JS
D000143:Acids / Q000737:chemistry; D000438:Alcohols / Q000737:chemistry; D018360:Crystallography, X-Ray; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D000078183:Oxindoles; D010165:Palladium / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000143:Acids; D000438:Alcohols; D007211:Indoles; D000078183:Oxindoles; D013141:Spiro Compounds; C022960:2-oxindole; D010165:Palladium