Stereoselective synthesis of spirocyclic oxindoles via Prins cyclizations.
The synthesis of spirocyclic oxindole pyran and oxepene frameworks using highly stereoselective Prins cyclizations of homoallylic and bis-homoallylic alcohols and isatin ketals is described.
Castaldi
M Paola
MP
Department of Chemistry and Center for Chemical Methodology and Library Development (CMLD-BU), Boston University, 590 Commonwealth Avenue, Boston, Massachusetts 02215, USA.
Troast
Dawn M
DM
Porco
John A
JA
D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D007510:Isatin / Q000737:chemistry; D010082:Oxepins / Q000138:chemical synthesis* / Q000737:chemistry; D000078183:Oxindoles; D020005:Propanols / Q000737:chemistry; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D012821:Silanes / Q000138:chemical synthesis* / Q000737:chemistry; D013141:Spiro Compounds / Q000737:chemistry; D013237:Stereoisomerism
D000475:Alkenes; D007211:Indoles; D010082:Oxepins; D000078183:Oxindoles; D020005:Propanols; D011714:Pyrans; D012821:Silanes; D013141:Spiro Compounds; C511847:allylsilane; C022960:2-oxindole; C006463:allyl alcohol; D007510:Isatin