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Asymmetric allylic alkylation of acyclic allylic ethers with organolithium reagents.
Chemistry. 2012 Sep 17; 18(38):11880-3.C

Abstract

A highly efficient, regio- and enantioselective Cu(I)/phosphoramidite-catalyzed asymmetric allylic alkylation of allyl ethers with organolithium reagents is reported (see scheme). The use of organolithium reagents is essential for this catalytic C-C bond formation due to their compatibility with different Lewis acids. The versatility of allylic ethers under the copper-catalyzed reaction conditions with organolithium reagents is demonstrated in the shortest synthesis of (S)-Arundic acid.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Pérez M
Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen, The Netherlands.
Fañanás-Mastral M
No affiliation info available
Hornillos V
No affiliation info available
Rudolph A
No affiliation info available
Bos PH
No affiliation info available
Harutyunyan SR
No affiliation info available
Feringa BL
No affiliation info available

MeSH

AlkylationAllyl CompoundsCaprylatesCatalysisCopperEthersIndicators and ReagentsLithium CompoundsMolecular StructureStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

22907628

Citation

Pérez, Manuel, et al. "Asymmetric Allylic Alkylation of Acyclic Allylic Ethers With Organolithium Reagents." Chemistry (Weinheim an Der Bergstrasse, Germany), vol. 18, no. 38, 2012, pp. 11880-3.
Pérez M, Fañanás-Mastral M, Hornillos V, et al. Asymmetric allylic alkylation of acyclic allylic ethers with organolithium reagents. Chemistry. 2012;18(38):11880-3.
Pérez, M., Fañanás-Mastral, M., Hornillos, V., Rudolph, A., Bos, P. H., Harutyunyan, S. R., & Feringa, B. L. (2012). Asymmetric allylic alkylation of acyclic allylic ethers with organolithium reagents. Chemistry (Weinheim an Der Bergstrasse, Germany), 18(38), 11880-3. https://doi.org/10.1002/chem.201202251
Pérez M, et al. Asymmetric Allylic Alkylation of Acyclic Allylic Ethers With Organolithium Reagents. Chemistry. 2012 Sep 17;18(38):11880-3. PubMed PMID: 22907628.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Asymmetric allylic alkylation of acyclic allylic ethers with organolithium reagents. AU - Pérez,Manuel, AU - Fañanás-Mastral,Martín, AU - Hornillos,Valentín, AU - Rudolph,Alena, AU - Bos,Pieter H, AU - Harutyunyan,Syuzanna R, AU - Feringa,Ben L, Y1 - 2012/08/21/ PY - 2012/06/25/received PY - 2012/8/22/entrez PY - 2012/8/22/pubmed PY - 2013/2/5/medline SP - 11880 EP - 3 JF - Chemistry (Weinheim an der Bergstrasse, Germany) JO - Chemistry VL - 18 IS - 38 N2 - A highly efficient, regio- and enantioselective Cu(I)/phosphoramidite-catalyzed asymmetric allylic alkylation of allyl ethers with organolithium reagents is reported (see scheme). The use of organolithium reagents is essential for this catalytic C-C bond formation due to their compatibility with different Lewis acids. The versatility of allylic ethers under the copper-catalyzed reaction conditions with organolithium reagents is demonstrated in the shortest synthesis of (S)-Arundic acid. SN - 1521-3765 UR - https://www.unboundmedicine.com/medline/citation/22907628/Asymmetric_allylic_alkylation_of_acyclic_allylic_ethers_with_organolithium_reagents_ L2 - https://doi.org/10.1002/chem.201202251 DB - PRIME DP - Unbound Medicine ER -