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Iridium-Catalyzed Regio- and Enantioselective Allylic Substitution of Trisubstituted Allylic Electrophiles.
Angew Chem Int Ed Engl. 2016 09 12; 55(38):11651-5.AC

Abstract

The first Ir-catalyzed enantioselective allylation of trisubstituted allylic electrophiles has been developed. Through modification of the leaving group of allylic electrophiles, we found that trisubstituted allylic phosphates are suitable electrophiles for asymmetric allylation. The reaction of allylic phosphates with enol silanes derived from dioxinones gave allylated products in good yields with high enantioselectivities.

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Authors+Show Affiliations

Chen M
Departments of Chemistry, University of California, Berkeley, CA, 94720, USA.
Hartwig JF
Departments of Chemistry, University of California, Berkeley, CA, 94720, USA. jhartwig@berkeley.edu.

MeSH

Allyl CompoundsCatalysisIridiumPhosphatesSilanesStereoisomerism

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural

Language

eng

PubMed ID

27531137

Citation

Chen, Ming, and John F. Hartwig. "Iridium-Catalyzed Regio- and Enantioselective Allylic Substitution of Trisubstituted Allylic Electrophiles." Angewandte Chemie (International Ed. in English), vol. 55, no. 38, 2016, pp. 11651-5.
Chen M, Hartwig JF. Iridium-Catalyzed Regio- and Enantioselective Allylic Substitution of Trisubstituted Allylic Electrophiles. Angew Chem Int Ed Engl. 2016;55(38):11651-5.
Chen, M., & Hartwig, J. F. (2016). Iridium-Catalyzed Regio- and Enantioselective Allylic Substitution of Trisubstituted Allylic Electrophiles. Angewandte Chemie (International Ed. in English), 55(38), 11651-5. https://doi.org/10.1002/anie.201607053
Chen M, Hartwig JF. Iridium-Catalyzed Regio- and Enantioselective Allylic Substitution of Trisubstituted Allylic Electrophiles. Angew Chem Int Ed Engl. 2016 09 12;55(38):11651-5. PubMed PMID: 27531137.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Iridium-Catalyzed Regio- and Enantioselective Allylic Substitution of Trisubstituted Allylic Electrophiles. AU - Chen,Ming, AU - Hartwig,John F, Y1 - 2016/08/17/ PY - 2016/07/20/received PY - 2016/8/18/entrez PY - 2016/8/18/pubmed PY - 2018/8/28/medline KW - 1,1′-substituted olefins KW - allylic asymmetric substitution KW - allylic phosphates KW - dioxinones KW - iridium catalysis SP - 11651 EP - 5 JF - Angewandte Chemie (International ed. in English) JO - Angew Chem Int Ed Engl VL - 55 IS - 38 N2 - The first Ir-catalyzed enantioselective allylation of trisubstituted allylic electrophiles has been developed. Through modification of the leaving group of allylic electrophiles, we found that trisubstituted allylic phosphates are suitable electrophiles for asymmetric allylation. The reaction of allylic phosphates with enol silanes derived from dioxinones gave allylated products in good yields with high enantioselectivities. SN - 1521-3773 UR - https://www.unboundmedicine.com/medline/citation/27531137/Iridium_Catalyzed_Regio__and_Enantioselective_Allylic_Substitution_of_Trisubstituted_Allylic_Electrophiles_ DB - PRIME DP - Unbound Medicine ER -