Heterocycle formation through aza-annulation: A stereochemically controlled route to (±)-lupinine

DOI: 10.1016/S0040-4039(00)60550-6

Source and publish data:

Tetrahedron Letters p. 215 - 218 (1993)

Update date:2022-07-30

Topics:

Authors:

Paulvannan

Schwarz Schwarz

Stille Stille

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Article abstract of DOI:10.1016/S0040-4039(00)60550-6

The aza-annulation of an acyclic β-enaminoester with acryloyl chloride was found to be a very efficient method for nitrogen heterocycle formation. Stereospecific hydrogenation of the unsaturated dihydropyridone generated from aza-annulation gave a single disubstituted lactam product. The cis stereochemical relationship of the substituents was confirmed by transformation of the lactam to (±)-lupinine.

Full text of DOI:10.1016/S0040-4039(00)60550-6

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