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Synthesis 2014; 46(18): 2506-2514
DOI: 10.1055/s-0033-1338629
DOI: 10.1055/s-0033-1338629
paper
A Novel Route to 6-Substituted Piperidin-3-ols via Domino Cyclization of 2-Hydroxy-6-phosphinyl-5-hexenyl Tosylates with Primary Amines: Synthesis of (±)-Pseudoconhydrine and (±)-epi-Pseudoconhydrine
Further Information
Publication History
Received: 02 March 2014
Accepted after revision: 04 April 2014
Publication Date:
23 June 2014 (online)

Abstract
2-Hydroxy-6-phosphinyl-5-hexenyl tosylates, oxirane ring-opening products derived from glycidyl tosylates and phosphinyl-substituted allyl anions, undergo domino SN2–Michael reactions with primary amines to give 6-phosphinylmethylpiperidin-3-ols. The phosphinyl unit can be used in Horner olefination reactions. This approach is applied to the synthesis of racemic pseudoconhydrine and its epimer.
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