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Enantioselective Synthesis of Dihydropyrans. Catalysis of Hetero Diels-Alder Reactions by Bis(oxazoline) Copper(II) Complexes

David A. Evans*, Jeffrey S. Johnson and Edward J. Olhava

*Department of Chemistry & Chemical Biology, Harvard University, Cambridge, Massachusetts 02138

D. A. Evans, J. S. Johnson, E. J. Olhava, J. Am. Chem. Soc., 2000, 122, 1635-1649.

DOI: 10.1021/ja992175i


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Abstract

C2-symmetric bis(oxazoline)-Cu(II) complexes catalyze the inverse electron demand hetero Diels-Alder reaction of α,β-unsaturated carbonyl compounds with electron-rich olefins in high diastereo- and enantioselectivity. α,β-Unsaturated acyl phosphonates and β,γ-unsaturated α-keto esters and amides are effective heterodienes, while enol ethers and sulfides function as heterodienophiles.


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Key Words

Diels-Alder reaction, 3,4-dihydro-2H-pyrans


ID: J48-Y2000