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Regio- and enantioselective iridium-catalyzed intermolecular allylic etherification of achiral allylic carbonates with phenoxides.
J Am Chem Soc. 2003 Mar 26; 125(12):3426-7.JA

Abstract

An enantioselective and regioselective iridium-catalyzed allylic etherification is described. The reaction of sodium and lithium aryloxides with achiral (E)-cinnamyl and terminal aliphatic allylic electrophiles in the presence of 2 mol % of an iridium-phosphoramidite complex provides chiral allylic aryl ethers in high yields and excellent levels of regio- and enantioselectivity. Lithium aryloxides containing a single substituent at an ortho, meta, or para position as well as sterically hindered phenoxides were tolerated. Reactions in THF displayed the most suitable balance of rate, regio-, and enantioselectivity. High ee's were also observed for the products from the reaction of alkyl (E)-allylic carbonates.

Authors+Show Affiliations

López F
Department of Chemistry, Yale University, P.O. Box 208107, New Haven, Connecticut 06520-8107, USA.
Ohmura T
No affiliation info available
Hartwig JF
No affiliation info available

MeSH

Allyl CompoundsCarbonatesCatalysisEthersIridiumOxidesStereoisomerism

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, P.H.S.

Language

eng

PubMed ID

12643693

Citation

López, Fernando, et al. "Regio- and Enantioselective Iridium-catalyzed Intermolecular Allylic Etherification of Achiral Allylic Carbonates With Phenoxides." Journal of the American Chemical Society, vol. 125, no. 12, 2003, pp. 3426-7.
López F, Ohmura T, Hartwig JF. Regio- and enantioselective iridium-catalyzed intermolecular allylic etherification of achiral allylic carbonates with phenoxides. J Am Chem Soc. 2003;125(12):3426-7.
López, F., Ohmura, T., & Hartwig, J. F. (2003). Regio- and enantioselective iridium-catalyzed intermolecular allylic etherification of achiral allylic carbonates with phenoxides. Journal of the American Chemical Society, 125(12), 3426-7.
López F, Ohmura T, Hartwig JF. Regio- and Enantioselective Iridium-catalyzed Intermolecular Allylic Etherification of Achiral Allylic Carbonates With Phenoxides. J Am Chem Soc. 2003 Mar 26;125(12):3426-7. PubMed PMID: 12643693.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Regio- and enantioselective iridium-catalyzed intermolecular allylic etherification of achiral allylic carbonates with phenoxides. AU - López,Fernando, AU - Ohmura,Toshimichi, AU - Hartwig,John F, PY - 2003/3/20/pubmed PY - 2003/5/7/medline PY - 2003/3/20/entrez SP - 3426 EP - 7 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 125 IS - 12 N2 - An enantioselective and regioselective iridium-catalyzed allylic etherification is described. The reaction of sodium and lithium aryloxides with achiral (E)-cinnamyl and terminal aliphatic allylic electrophiles in the presence of 2 mol % of an iridium-phosphoramidite complex provides chiral allylic aryl ethers in high yields and excellent levels of regio- and enantioselectivity. Lithium aryloxides containing a single substituent at an ortho, meta, or para position as well as sterically hindered phenoxides were tolerated. Reactions in THF displayed the most suitable balance of rate, regio-, and enantioselectivity. High ee's were also observed for the products from the reaction of alkyl (E)-allylic carbonates. SN - 0002-7863 UR - https://www.unboundmedicine.com/medline/citation/12643693/Regio__and_enantioselective_iridium_catalyzed_intermolecular_allylic_etherification_of_achiral_allylic_carbonates_with_phenoxides_ DB - PRIME DP - Unbound Medicine ER -