ASYMMETRIC MICHAEL ADDITION/LACTAMIZATION VIA SAMP-/RAMP-HYDRAZONES ENANTIOSELECTIVE SYNTHESIS OF SUBSTITUTED TETRAHYDRO-2,5(1H,3H)-QUINOLINEDIONES

DOI: 10.1016/S0040-4039(00)96386-X

Source and publish data:

Tetrahedron Letters p. 3795 - 3798 (1987)

Update date:2022-07-29

Topics:

Authors:

Enders, Dieter

Demir, Ayhan S.

Puff, Heinrich

Franken, Sybille

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Article abstract of DOI:10.1016/S0040-4039(00)96386-X

An efficient and highly diastereo- and enantioselective annulation of cyclic 1.3-diketones to tetrahydro-quinolinediones of type 4 and 5 in good overall yields is described.The key step is the Michael addition of the corresponding lithiated SAMP-/RAMP-hydrazones to arylidenemalonates followed by lactamization with virtually complete asymmetric induction (de,ee<*>98percent).

Full text of DOI:10.1016/S0040-4039(00)96386-X

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