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The use of silyl ketene acetals and enol ethers in the catalytic enantioselective alkylative ring opening of oxa/aza bicyclic alkenes.
Angew Chem Int Ed Engl. 2014 Jun 02; 53(23):5951-4.AC

Abstract

Silyl ketene acetals and enol ethers are employed as reactive and functional group tolerant nucleophiles in the enantioselective rhodium-catalyzed alkylative ring opening of a diverse class of oxa/azabicyclic alkenes. This method provides access to enantioenriched dihydronaphthalene and cyclohexene scaffolds, which have the potential to be derivatized toward core motifs of naphthoquinone and sesquiterpene natural products.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Zhang L
Davenport Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, ON, M5S 3H6 (Canada).
Le CM
No affiliation info available
Lautens M
No affiliation info available

MeSH

AcetalsAlkenesCatalysisEthersEthylenesKetonesStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

24771670

Citation

Zhang, Lei, et al. "The Use of Silyl Ketene Acetals and Enol Ethers in the Catalytic Enantioselective Alkylative Ring Opening of Oxa/aza Bicyclic Alkenes." Angewandte Chemie (International Ed. in English), vol. 53, no. 23, 2014, pp. 5951-4.
Zhang L, Le CM, Lautens M. The use of silyl ketene acetals and enol ethers in the catalytic enantioselective alkylative ring opening of oxa/aza bicyclic alkenes. Angew Chem Int Ed Engl. 2014;53(23):5951-4.
Zhang, L., Le, C. M., & Lautens, M. (2014). The use of silyl ketene acetals and enol ethers in the catalytic enantioselective alkylative ring opening of oxa/aza bicyclic alkenes. Angewandte Chemie (International Ed. in English), 53(23), 5951-4. https://doi.org/10.1002/anie.201400218
Zhang L, Le CM, Lautens M. The Use of Silyl Ketene Acetals and Enol Ethers in the Catalytic Enantioselective Alkylative Ring Opening of Oxa/aza Bicyclic Alkenes. Angew Chem Int Ed Engl. 2014 Jun 2;53(23):5951-4. PubMed PMID: 24771670.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - The use of silyl ketene acetals and enol ethers in the catalytic enantioselective alkylative ring opening of oxa/aza bicyclic alkenes. AU - Zhang,Lei, AU - Le,Christine M, AU - Lautens,Mark, Y1 - 2014/04/25/ PY - 2014/01/08/received PY - 2014/4/29/entrez PY - 2014/4/29/pubmed PY - 2015/4/22/medline KW - asymmetric catalysis KW - rhodium KW - silyl ketene acetals KW - strained molecules SP - 5951 EP - 4 JF - Angewandte Chemie (International ed. in English) JO - Angew Chem Int Ed Engl VL - 53 IS - 23 N2 - Silyl ketene acetals and enol ethers are employed as reactive and functional group tolerant nucleophiles in the enantioselective rhodium-catalyzed alkylative ring opening of a diverse class of oxa/azabicyclic alkenes. This method provides access to enantioenriched dihydronaphthalene and cyclohexene scaffolds, which have the potential to be derivatized toward core motifs of naphthoquinone and sesquiterpene natural products. SN - 1521-3773 UR - https://www.unboundmedicine.com/medline/citation/24771670/The_use_of_silyl_ketene_acetals_and_enol_ethers_in_the_catalytic_enantioselective_alkylative_ring_opening_of_oxa/aza_bicyclic_alkenes_ DB - PRIME DP - Unbound Medicine ER -