B(C6F5)3-Promoted Tandem Silylation and Intramolecular Hydrosilylation: Diastereoselective Synthesis of Oxasilinanes and Oxasilepanes
- 4 October 2010
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 12 (21), 4772-4775
- https://doi.org/10.1021/ol1018757
Abstract
B(C6F5)3 promotes regio- and stereoselective cyclizations of unsaturated alkoxysilanes to generate oxasilinanes and oxasilepanes. The same products are available directly from alkenols via tandem silylation and hydrosilylation.Keywords
This publication has 26 references indexed in Scilit:
- Stereoselective Synthesis of syn,syn- and syn,anti-1,3,5-Triols via Intramolecular Hydrosilylation of Substituted Pent-3-en-1,5-diolsOrganic Letters, 2009
- Fully Reagent-Controlled Asymmetric Synthesis of (−)-Spongidepsin via the Zr-Catalyzed Asymmetric Carboalumination of Alkenes (ZACA Reaction)Organic Letters, 2007
- Mechanism of the B(C6F5)3-Catalyzed Reaction of Silyl Hydrides with Alkoxysilanes. Kinetic and Spectroscopic StudiesOrganometallics, 2005
- Tris(pentafluorophenyl)borane: a special boron Lewis acid for special reactionsDalton Transactions, 2005
- A metal-free catalytic intramolecular hydrosilylationCanadian Journal of Chemistry, 2003
- Highly Efficient B(C6F5)3-Catalyzed Hydrosilylation of OlefinsThe Journal of Organic Chemistry, 2002
- Palladium-Catalyzed Intramolecular Hydrosilylation of Alkenylsilanes: Selective Formation of Six-Membered Silicon HeterocyclesOrganometallics, 1998
- Intramolecular radical-chain hydrosilylation catalysed by thiols: cyclisation of alkenyloxysilanesJournal of the Chemical Society, Perkin Transactions 1, 1998
- Chirality transmission involving a free-radical-mediated 6-exo cyclization process. Stereocontrolled synthesis of branched-chain 1,4-diolsJournal of the American Chemical Society, 1990
- Organic chemistry of dichlorosilane. Additions to conjugated and unconjugated diene systems followed by intramolecular cyclizationsThe Journal of Organic Chemistry, 1979