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Flexible strategy for syntheses of spirooxindoles using palladium-catalyzed carbosilylation and Sakurai-type cyclization.
- Source :
-
Organic letters [Org Lett] 2011 Apr 01; Vol. 13 (7), pp. 1828-31. Date of Electronic Publication: 2011 Mar 08. - Publication Year :
- 2011
-
Abstract
- The intramolecular carbosilylation of N-[2-(1,3-butenyl)aryl]carbamoyl chloride has been investigated. The reaction with hexamethyldisilane proceeds smoothly in the presence of a catalytic amount of [Pd(η(3)-allyl)Cl](2) to give oxindoles with an allylsilane functional group in good yield. The subsequent subjection of the products to a Sakurai-type reaction provides more advanced tricyclic spirooxindoles by controlling the stereochemistry of three contiguous stereogenic centers.
Details
- Language :
- English
- ISSN :
- 1523-7052
- Volume :
- 13
- Issue :
- 7
- Database :
- MEDLINE
- Journal :
- Organic letters
- Publication Type :
- Academic Journal
- Accession number :
- 21384892
- Full Text :
- https://doi.org/10.1021/ol2003447