HETERO-COPE REARRANGEMENTS - VI; SHORT AND STEREOSELECTIVE SYNTHESIS OF 2-VINYLINDOLES BY A TANDEM-PROCESS

DOI: 10.1016/S0040-4020(01)90291-1

Source and publish data:

Tetrahedron p. 3237 - 3246 (1987)

Update date:2022-08-05

Topics:

Authors:

Wilkens, Jochen

Kuehling, Andrea

Blechert, Siegfried

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Article abstract of DOI:10.1016/S0040-4020(01)90291-1

The initially formed N-phenylnitrone-intermediates are converted by a tandem-reaction (cycloaddition, Cope rearrangement, retro-Michael addition, and indolization) to 2-vinylindoles 7.Thus these indoles can be synthesized simply and stereoselectively in a one-pot reaction from N-phenylhydroxylamine 4, aldehydes 5, and electrondeficient allenes 6.

Full text of DOI:10.1016/S0040-4020(01)90291-1

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