Tags

Type your tag names separated by a space and hit enter

Enantioselective Synthesis of Vicinal All-Carbon Quaternary Centers via Iridium-Catalyzed Allylic Alkylation.
Angew Chem Int Ed Engl. 2018 07 09; 57(28):8664-8667.AC

Abstract

The development of the first enantioselective transition-metal-catalyzed allylic alkylation providing access to acyclic products bearing vicinal all-carbon quaternary centers is disclosed. The iridium-catalyzed allylic alkylation reaction proceeds with excellent yields and selectivities for a range of malononitrile-derived nucleophiles and trisubstituted allylic electrophiles. The utility of these sterically congested products is explored through a series of diverse chemo- and diastereoselective product transformations to afford a number of highly valuable, densely functionalized building blocks, including those containing vicinal all-carbon quaternary stereocenters.

Links

PMC Free PDF

Authors+Show Affiliations

Hethcox JC
The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 E. California Blvd, MC 101-20, Pasadena, CA, 91125, USA.
Shockley SE
The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 E. California Blvd, MC 101-20, Pasadena, CA, 91125, USA.
Stoltz BM
The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 E. California Blvd, MC 101-20, Pasadena, CA, 91125, USA.

MeSH

AlkylationAllyl CompoundsCarbonCatalysisIridiumMolecular StructureStereoisomerism

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

29750856

Citation

Hethcox, J Caleb, et al. "Enantioselective Synthesis of Vicinal All-Carbon Quaternary Centers Via Iridium-Catalyzed Allylic Alkylation." Angewandte Chemie (International Ed. in English), vol. 57, no. 28, 2018, pp. 8664-8667.
Hethcox JC, Shockley SE, Stoltz BM. Enantioselective Synthesis of Vicinal All-Carbon Quaternary Centers via Iridium-Catalyzed Allylic Alkylation. Angew Chem Int Ed Engl. 2018;57(28):8664-8667.
Hethcox, J. C., Shockley, S. E., & Stoltz, B. M. (2018). Enantioselective Synthesis of Vicinal All-Carbon Quaternary Centers via Iridium-Catalyzed Allylic Alkylation. Angewandte Chemie (International Ed. in English), 57(28), 8664-8667. https://doi.org/10.1002/anie.201804820
Hethcox JC, Shockley SE, Stoltz BM. Enantioselective Synthesis of Vicinal All-Carbon Quaternary Centers Via Iridium-Catalyzed Allylic Alkylation. Angew Chem Int Ed Engl. 2018 07 9;57(28):8664-8667. PubMed PMID: 29750856.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Enantioselective Synthesis of Vicinal All-Carbon Quaternary Centers via Iridium-Catalyzed Allylic Alkylation. AU - Hethcox,J Caleb, AU - Shockley,Samantha E, AU - Stoltz,Brian M, Y1 - 2018/06/11/ PY - 2018/04/25/received PY - 2018/5/12/pubmed PY - 2019/7/28/medline PY - 2018/5/12/entrez KW - allylic alkylation KW - enantioselective synthesis KW - iridium KW - quaternary stereocenters KW - transition-metal catalysis SP - 8664 EP - 8667 JF - Angewandte Chemie (International ed. in English) JO - Angew Chem Int Ed Engl VL - 57 IS - 28 N2 - The development of the first enantioselective transition-metal-catalyzed allylic alkylation providing access to acyclic products bearing vicinal all-carbon quaternary centers is disclosed. The iridium-catalyzed allylic alkylation reaction proceeds with excellent yields and selectivities for a range of malononitrile-derived nucleophiles and trisubstituted allylic electrophiles. The utility of these sterically congested products is explored through a series of diverse chemo- and diastereoselective product transformations to afford a number of highly valuable, densely functionalized building blocks, including those containing vicinal all-carbon quaternary stereocenters. SN - 1521-3773 UR - https://www.unboundmedicine.com/medline/citation/29750856/Enantioselective_Synthesis_of_Vicinal_All_Carbon_Quaternary_Centers_via_Iridium_Catalyzed_Allylic_Alkylation_ DB - PRIME DP - Unbound Medicine ER -