Tetrahedron Letters p. 7491 - 7494 (1998)
Update date:2022-08-05
Topics:
Stephen
Hashmi
Bats, Jan W.
Choi, Ji-Hyun
Schwarz, Lothar
Dess-Martin oxidation followed by the chromatographic workup of crude, terminal propargyl ketones 5 on silica gel directly leads to terminal allenyl ketones 6. When the other substituent on 5 was electron-rich, 7 was observed as side-product. If the other substituent on 5 was electron-poor, the isomeric 1-propynyl ketone 8 was the side-product. Chromatography of the crude propargyl vinyl ketones 10 on silica gel delivers the products of a Nazarov cyclization.
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