Enantiospecific and regioselective rhodium-catalyzed allylic alkylation: diastereoselective approach to quaternary carbon stereogenic centers
- PMID: 10930246
- DOI: 10.1021/ol005953g
Enantiospecific and regioselective rhodium-catalyzed allylic alkylation: diastereoselective approach to quaternary carbon stereogenic centers
Abstract
The enantiospecific and regioselective rhodium-catalyzed allylic alkylation of a series of chiral nonracemic allylic carbonates, followed by ozonolysis and reductive lactonization, provides a convenient route to optically active gamma-lactones. Sequential alkylation and reductive alkylation furnished the alpha-quaternary-beta-ternary substituted gamma-lactone derivative as a >/=10:1 mixture of diastereoisomers.
Similar articles
-
Regio- and enantiospecific rhodium-catalyzed arylation of unsymmetrical fluorinated acyclic allylic carbonates: inversion of absolute configuration.J Am Chem Soc. 2003 Jun 18;125(24):7158-9. doi: 10.1021/ja035216q. J Am Chem Soc. 2003. PMID: 12797772 Free PMC article.
-
Regioselective and enantiospecific rhodium-catalyzed allylic alkylation reactions using copper(I) enolates: synthesis of (-)-sugiresinol dimethyl ether.J Am Chem Soc. 2003 Jul 30;125(30):8974-5. doi: 10.1021/ja035983p. J Am Chem Soc. 2003. PMID: 15369328
-
Features and applications of [Rh(CO)(2)Cl](2)-catalyzed alkylations of unsymmetrical allylic substrates.J Org Chem. 2007 Nov 23;72(24):9018-31. doi: 10.1021/jo701290b. Epub 2007 Nov 1. J Org Chem. 2007. PMID: 17973524
-
Asymmetric Rhodium-Catalyzed Allylic Substitution Reactions: Discovery, Development and Applications to Target-Directed Synthesis.J Org Chem. 2018 Oct 5;83(19):11463-11479. doi: 10.1021/acs.joc.8b00583. Epub 2018 Sep 5. J Org Chem. 2018. PMID: 30183287 Review.
-
Rhodium-catalyzed C-C bond formation via heteroatom-directed C-H bond activation.Chem Rev. 2010 Feb 10;110(2):624-55. doi: 10.1021/cr900005n. Chem Rev. 2010. PMID: 19438203 Free PMC article. Review. No abstract available.
Cited by
-
Recent Developments in Rhodium-Catalyzed Allylic Substitution and Carbocyclization Reactions.Chemtracts. 2003 Aug 1;16(9):567-578. Chemtracts. 2003. PMID: 17047733 Free PMC article. No abstract available.
-
De novo asymmetric Achmatowicz approach to oligosaccharide natural products.Chem Commun (Camb). 2022 Nov 22;58(93):12913-12926. doi: 10.1039/d2cc05280f. Chem Commun (Camb). 2022. PMID: 36321854 Free PMC article. Review.
-
Rhodium-catalysed asymmetric allylic arylation of racemic halides with arylboronic acids.Nat Chem. 2015 Nov;7(11):935-9. doi: 10.1038/nchem.2360. Epub 2015 Oct 12. Nat Chem. 2015. PMID: 26492015
Publication types
MeSH terms
Substances
Grants and funding
LinkOut - more resources
Full Text Sources