Highly enantioselective catalytic asymmetric Claisen rearrangement of 2-alkoxycarbonyl-substituted allyl vinyl ethers

Tetrahedron Letters

Volumn 45, Issue 18, 2004, Pages 3647-3650

  Abraham, Lars ^a   Körner, Marleen ^a   Hiersemann, Martin ^a  

^a DRESDEN UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

Asymmetric catalysis; Claisen rearrangement; Copper(II) bis(oxazoline); Lewis acid

Indexed keywords

ALPHA KETO ESTER; ETHER DERIVATIVE; LEWIS ACID; UNCLASSIFIED DRUG;

ACIDITY; ARTICLE; CATALYSIS; CATALYST; CHIRALITY; CLAISEN REARRANGEMENT; ENANTIOMER; ENANTIOSELECTIVITY; EXPERIMENT; POLARIZATION;

EID: 1842635738     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.03.047     Document Type: Article

References (19)

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11. For a less successful Lewis acid-catalyzed asymmetric Claisen rearrangement, see: Helmboldt H., Hiersemann M. Tetrahedron. 59:2003;4031-4038.
12. Evans D.A., Tregay S.W., Burgey C.S., Paras N.A., Vojkovsky T. J. Am. Chem. Soc. 122:2000;7936-7943.
13. 2-Alkoxycarbonyl-substituted allyl vinyl ethers 2 were synthesized according to our previously published procedure: Hiersemann M. Synthesis. 2000;1279-1290. The vinyl ether double bond isomers have been separated by preparative HPLC. Details will be published elsewhere.
14. 1 A careful reinvestigation using a new charge of ligand and allyl vinyl ether (Z)-1c in the presence of molecular sieves afforded the rearrangement product 2c with an increased enantioselectivity.
15. 3: C, 65.19; H, 8.75. Found: C, 65.22; H, 8.84.
16. 4Si: C, 71.19; H, 7.81. Found: C, 71.01, H, 7.84.
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