Novel and stereocontrolled synthesis of enantiopure and polyalkyl substituted piperidines

Synlett

Volumn , Issue 6, 1998, Pages 652-654

  Schneider, Christoph ^a   Börner, Christoph ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 26844456896     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1725     Document Type: Article

References (43)

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35. 3: C 74.26, H 7.67; found C 74.54, H 7.56.
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37. 2 and treated with 0.14 ml (1.10 mmol) TMSCN for 2 h at rt. After evaporation of the solvent and Chromatographie purification on silica gel (ether/petroleum ether = 2:1) 270 mg (90%) of the amino nitrite 6b are obtained. Cyclization of 6b is accomplished with 0.42 ml (1.00 mmol) of triton B (40% in methanol) in 5 ml methanol for 12 h at rt. Aqueous workup and chromatographic purification (silica gel, ether/petroleum ether = 1:2) gave 243 mg (90%) of the cyano piperidine 7b. The piperidine is dissolved in 5 ml dry THF and treated with 228 mg (0.90 mmol) silver triflate for 5 min at rt. An allyl zinc bromide solution made of 160 mg (2.43 mmol) zinc dust and 0.10 ml (1.20 mmol) allyl bromide in 5 ml DMF is added at 0°C and stirring is continued for 10 min at 0°C. Aqueous workup and cromatographic purification (silica gel, ether/petroleum ether = 1:2) gave 198 mg (78%) of the piperidine 9a.
38. 6-α-configurated isomer from the mixture and treating it again with triton B in methanol leads to a complete epimerization at C-6.
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42. 2: C 76.15, H 9.27; found C 75.92, H 9.44.
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