An efficient FeCl(3)-catalyzed stereoselective intramolecular tandem 1,5-hydride transfer/ring closure reaction was developed. The method allows for the formation of structurally diverse spirooxindole tetrahydroquinolines in high yields (up to 98%) with good to excellent levels of diastereoselectivity (up to 99:1 dr). The catalytic enantioselective variant of this process was also investigated preliminarily with a chiral BINOL-derived phosphoric acid.
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http://dx.doi.org/10.1021/ol301559k | DOI Listing |
J Am Chem Soc
October 2012
Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, People's Republic of China.
The completely OH-selective Prins cyclization has been realized from the enantioselective ene reaction product. A variety of 4-hydroxyl-tetrahydropyrans were exclusively generated via FeCl(3)-catalyzed Prins reaction. Excellent stereoselectivities (up to >99:1 dr and >99.
View Article and Find Full Text PDFOrg Lett
August 2012
National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China.
An efficient FeCl(3)-catalyzed stereoselective intramolecular tandem 1,5-hydride transfer/ring closure reaction was developed. The method allows for the formation of structurally diverse spirooxindole tetrahydroquinolines in high yields (up to 98%) with good to excellent levels of diastereoselectivity (up to 99:1 dr). The catalytic enantioselective variant of this process was also investigated preliminarily with a chiral BINOL-derived phosphoric acid.
View Article and Find Full Text PDFCarbohydr Res
December 2008
State Key Laboratory of Environmental Chemistry and Ecotoxicology, Research Center for Eco-Environmental Scienece, Chinese Academy of Sciences, Beijing 100085, China.
An efficient method for the large-scale preparation of alpha-N-acetylglycosaminides, such as fluorogenic T(N)-antigen probes and an alpha-GalNAc-Ser derivative, has been achieved using FeCl(3)-catalyzed one-step condensation between commercially available D-glycosamine pentaacetates and fluorogenic acceptors (or serine acceptor) in refluxing 1,2-dichloroethane. Experimental simplicity, high alpha-stereoselectivity, low cost, satisfactory yield, and the environmentally benign nature are major advantages of our approach.
View Article and Find Full Text PDFOrg Lett
February 2006
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, 354 Fenglin Lu, Shanghai 200032, China.
[reaction: see text] The aminochlorination of methylenecyclopropanes (MCPs) 1 and vinylidenecyclopropanes (VCPs) has been explored with use of FeCl(3) (20 mol %) as a Lewis acid catalyst in acetonitrile under convenient mild conditions. The stereochemistry has been unambiguously confirmed by X-ray structural analysis. The aziridinium-based mechanism, accounting for both regio- and stereoselectivity, has been carefully studied.
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