Desymmetrization of Hepta-1,6-dien-4-ol by a Highly Stereo­selective Tandem Prins–Ritter Cyclization: Access to New THP Acetamides

Desymmetrization of Hepta-1,6-dien-4-ol by a Highly Stereo­selective Tandem Prins–Ritter Cyclization: Access to New THP Acetamides

Abstract Prins–Ritter cyclization performed from hepta-1,6-dien-4-ol and various aldehydes, promoted by bismuth(II) triflate, afforded N -(tetrahydropyranyl)acetamides in moderate to high yields. Subsequent Wacker-type oxidation using Dess–Martin periodinane (DMP) delivered the corresponding ketones...

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Veröffentlicht in:Synthesis (Stuttgart) 2017-12, Vol.49 (23), p.5197-5202
Hauptverfasser: Glachet, Thomas, Fache, Fabienne, Pelotier, Béatrice, Piva, Olivier
Format: Artikel
Sprache:eng
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Zusammenfassung:Abstract Prins–Ritter cyclization performed from hepta-1,6-dien-4-ol and various aldehydes, promoted by bismuth(II) triflate, afforded N -(tetrahydropyranyl)acetamides in moderate to high yields. Subsequent Wacker-type oxidation using Dess–Martin periodinane (DMP) delivered the corresponding ketones.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0036-1588521