Enantioselective Arylative Cyclization of Allenyl Aldehydes with Arylboronic Acids under Pd(II)-diphosphine Catalysis
- 23 February 2008
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 10 (6), 1047-1050
- https://doi.org/10.1021/ol702966j
Abstract
A Pd(OAc)2−SEGPHOS combination catalyzes the first enantioselective arylative cyclization of allenyl aldehydes with arylboronic acids to provide cis-fused five- and six-membered cyclic homoallylic alcohols. The excellent diastereo- and enantioselectivity and the fact that the reaction proceeds at room temperature in the absence of any additives make the process highly practical.Keywords
This publication has 20 references indexed in Scilit:
- Microwave-Assisted Palladium(0)-Catalyzed Alkylative Cyclization of Allenyl Aldehydes Leading to 3-Substituted 3-Cycloalken-1-olsJournal of the American Chemical Society, 2007
- Rhodium-catalyzed arylative cyclization of alkynones induced by addition of arylboronic acidsTetrahedron, 2007
- Allylpalladium Umpolung in the Three-Component Coupling Synthesis of Homoallylic AminesOrganic Letters, 2006
- Palladium(0)-Catalyzed Alkylative Cyclization of Alkynals and Alkynones: Remarkable trans-Addition of Organoboronic ReagentsJournal of the American Chemical Society, 2006
- Acyl 1,3‐Migration in Rhodium‐Catalyzed Reactions of Acetylenic β‐Ketoesters with Aryl Boronic Acids: Application to Two‐Carbon‐Atom Ring ExpansionsAngewandte Chemie-International Edition, 2005
- Regiocontrolled, Palladium-Catalyzed Bisfunctionalization of Allenyl Esters. Multicomponent Coupling Approaches to Highly Substituted α,β-Unsaturated δ-LactonesThe Journal of Organic Chemistry, 2005
- Synthesis of Seven‐Membered‐Ring Ketones by Arylative Ring Expansion of Alkyne‐Substituted CyclobutanonesAngewandte Chemie-International Edition, 2005
- Synthesis of Homoallylic Alcohols via Palladium-Catalyzed Three-Component Coupling of an Arylboronic Acid with Allenes and AldehydesOrganic Letters, 2004
- Rhodium-Catalyzed Asymmetric 1,4-Addition and Its Related Asymmetric ReactionsChemical Reviews, 2003
- Rhodium-Catalyzed Carbon−Carbon Bond Forming Reactions of Organometallic CompoundsChemical Reviews, 2002