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

Scherner Cathrin; Ergueden Jens Kerim; Adiwidjaja Gunadi; Schaumann Ernst<sup>*</sup>

doi:10.1055/s-0033-1338629

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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

作者：Scherner Cathrin; Ergueden Jens Kerim; Adiwidjaja Gunadi; Schaumann Ernst^*

来源：Synthesis (Germany), 2014, 46(18): 2506-2514.

DOI：10.1055/s-0033-1338629

摘要

2-Hydroxy-6-phosphinyl-5-hexenyl tosylates, oxirane ring-opening products derived from glycidyl tosylates and phosphinyl-substituted allyl anions, undergo domino S(N)2-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.