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Synthesis 2017; 49(23): 5197-5202
DOI: 10.1055/s-0036-1588521
DOI: 10.1055/s-0036-1588521
paper
Desymmetrization of Hepta-1,6-dien-4-ol by a Highly Stereoselective Tandem Prins–Ritter Cyclization: Access to New THP Acetamides
Further Information
Publication History
Received: 10 May 2017
Accepted after revision: 05 July 2017
Publication Date:
14 August 2017 (online)
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.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1588521.
- Supporting Information
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For recent syntheses of diospongin A and stereomers:
For a recent review on Ritter reactions, see: