en
Scientific article
English

Enantioselective preparation and hydroboration of cyclic enamides: Synthesis of (2S)-pseudoconhydrine

Published inTetrahedron letters, vol. 36, no. 17, p. 2959-2962
Publication date1995-04-24
First online date2000-06-14
Abstract

Successive treatment of 2-alkyl-1-hydroxy-6-carbonylsultampiperidines 1 with NaH and an acylating agent/pyridine in boiling toluene affords optically pure 1-acyl-2-alkyl-1,2,3,4-tetrahydropyridines 2. Hydroboration/oxidation of N-benzoylenamides 2f and 2g furnishes trans-2-alkyl-1-benzyl-5-hydroxypiperidines5f and 5g, respectively. Hydrogenolysis of 5f provides pure (2S)-pseudoconhydrine (7), in 3 steps from 1, R2=n-C3H7 (31 % overall yield).

eng
Citation (ISO format)
VON OPPOLZER, Wolfgang, BOCHET, Christian. Enantioselective preparation and hydroboration of cyclic enamides: Synthesis of (2S)-pseudoconhydrine. In: Tetrahedron letters, 1995, vol. 36, n° 17, p. 2959–2962. doi: 10.1016/0040-4039(95)00439-j
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ISSN of the journal0040-4039
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