Ritter reaction on terpenoids. III. Stereospecific preparation of bicyclic [3.3.1] substituted piperidines

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Treatment of chiral monoterpenes with different nitrile compounds in the presence of perchloric acid affords (1S,5R,8R) 8-alkyl(aryl)-2-alkyl(aryl)-2,4,4,8-tetramethyl-3-azabicyclo[3.3.1]non-2-ene or the corresponding (1R,5S,8S) enantiomer. The respective free imines yield optically pure piperidine...

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Detalles Bibliográficos
Autor principal: Samaniego, W.N
Otros Autores: Baldessari, A., Ponce, M.A, Rodriguez, J.B, Gros, E.G, Caram, J.A, Marschoff, C.M
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: 1994
Acceso en línea:Registro en Scopus
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024 7 |2 scopus  |a 2-s2.0-0028137246 
040 |a Scopus  |b spa  |c AR-BaUEN  |d AR-BaUEN 
030 |a TELEA 
100 1 |a Samaniego, W.N. 
245 1 0 |a Ritter reaction on terpenoids. III. Stereospecific preparation of bicyclic [3.3.1] substituted piperidines 
260 |c 1994 
270 1 0 |m Samaniego, W.N.; Departamento de Química Orgánica, Facultad de Ciencias Exactas, Universidad de Buenos Aires, Pabellon 2, Ciudad Universitaria, 1428 Buenos Aires, Argentina 
506 |2 openaire  |e Política editorial 
504 |a Caram, Martins, Marschoff, Cafferata, Gros, (1984) Z. Naturforsch., 39 b, p. 972 
504 |a Ritter, Minieri, (1948) J. Am. Chem. Soc., 70, p. 4045 
504 |a Krimen, Cota, (1969) Org. React., 17, p. 213 
504 |a Johnson, Madroñero, (1966) Adv. Heterocycl. Chem., 6, p. 95 
504 |a Caram, Rivero, Piro, Gros, Marschoff, On the unusual hydrolysis reaction of 8-acetamido-2,4,4,8-tetramethyl-3-azanium-bicyclo[3.3.1]non-2-ene perchlorate (1990) Canadian Journal of Chemistry, 68, p. 334 
504 |a Viturro, Rivero, Piro, Caram, Martins, Marschoff, Crystal and molecular structure of 8-acetamido-2,4,4,8-tetramethyl-3-azaniumbicyclo[3.3.1]non-2-ene perchlorate (1987) Canadian Journal of Chemistry, 65, p. 2000 
504 |a Bong, Ung, Craig, Scudder, Bishop, Ritter Reactions. V. Further Investigation of the 3-Azatricyclo[5.3.1.04,9]undec-2-ene System (1989) Australian Journal of Chemistry, 42, p. 1929 
504 |a Bishop, Hawkings, Ibana, (1988) J. Org. Chem., 53, p. 427 
504 |a A mixture of terpene (2 mmol) and nitrile (20 mmol) was warmed until melting was complete (when solid nitriles were employed) with vigorous stirring (starting materials and reaction temperatures are indicated in Table 1). Then, concentrated perchloric acid (0.1 ml) was added dropwise and the reaction mixture was stirred overnight at the same temperature. The mixture was allowed to cool and ethyl acetate (10 ml) was added. The white precipitate was filtered off and crystallized from ethanol. Yields fluctuated between 12–36%; 1(S),5(R),8(R)-8-Benzamido-2-phenyl-4,4,8-trymethyl-3-azabicyclo[3.3.1]non-2-ene (2a)mp = 210–212°C. [α]D = −231.5 (0.9, MeOH). IR (Nujol, cm−1) 3350, 2310, 1635, 1615, 1590, 1100, 735, 700, 620. 1H-NMR (DMSO-d6) δ 0.88 (s, 3H, CH3 at C-8), 1.50 (s, 3H, CH3 at C-4), 1.61 (s, 3H, CH3 at C-4), 1.70–2.20 (bs, 8H, H-1, H-5, H-6, H-7 & H-9), 5.03 (bs, 1H, CNH+), 7.40–8.16 (m, 10H, aromatic protons). 13C-NMR (DMSO-d6) δ 21.65 (CH3 at C-4), 23.26 (CH3 at C-4), 25.66 (C-7), 28.50 (C-6 and Me at C-8), 31.28 (C-9), 33.51 (C-5), 38.83 (C-1), 56.37 (C-8), 62.13 (C-4), 127.28 (Ph), 127.93 (Ph), 128.89 (Ph), 128.96 (Ph), 129.24 (Ph), 131.03 (Ph), 133.08 (Ph), 133.30 (Ph), 134.35 (Ph), 134.98 (Ph), 167.23, PhC[[Truncated]]; Harada, (1970) The Chemistry of the Carbon-Nitrogen Double Bond, pp. 276-293. , S. Patai, Wiley, New York 
504 |a Anderson, Robertson, Avey, Donovan, Bick, Bremner, Finney, Russell, Aristoteline, a novel indole alkaloid: X-ray structural determination (1975) Journal of the Chemical Society, Chemical Communications, p. 511. , These synthetic compounds are closely related to naturally occurring alkaloids, for example, aristoteline, isolated from Aristotelia serrata, Aristotelia peduncularis and from the leaves and stems of Aristotelia chilensis 
504 |a Kyburz, Schöpp, Bick, Hesse, (1981) Helv. Chim. Acta, 64, p. 2555 
504 |a Bhakuni, Silva, Matlin, Sammes, (1976) Phytochemistry, 15, p. 574 
504 |a Bick, Hai, Preston, Gallagher, (1980) Tetrahedron Lett., 21, p. 545. , aristotelinona, isolated from A. serrata 
504 |a Kyburz, Schöpp, Hesse, Peduncularistin, Triabunnin und Aristolarin, drei neue Indolalkaloide ausAristotelia peduncularis (LABILL.) HOOK. F., 191. Mitteilung �ber organische Naturstoffe (1984) Helvetica Chimica Acta, 67, p. 804. , tasmanine, isolated from A. peduncularis12b; serratoline, isolated from A. serrata 
504 |a Kyburz, Schöpp, Bick, Hesse, (1979) Helv. Chim. Acta, 62, p. 2539. , hobartine, isolated from A. peduncularis 
520 3 |a Treatment of chiral monoterpenes with different nitrile compounds in the presence of perchloric acid affords (1S,5R,8R) 8-alkyl(aryl)-2-alkyl(aryl)-2,4,4,8-tetramethyl-3-azabicyclo[3.3.1]non-2-ene or the corresponding (1R,5S,8S) enantiomer. The respective free imines yield optically pure piperidine derivatives when treated with reducing agents (NaBH4, NaCNBH3). © 1990.  |l eng 
593 |a Departamento de Química Orgánica, Facultad de Ciencias Exactas, Universidad de Buenos Aires, Pabellon 2, Ciudad Universitaria, 1428 Buenos Aires, Argentina 
593 |a División Eletroquímica, Instutito de Investigaciones Fisicoquímicas Teóricas y Aplicadas (INIFTA), C.C. 16, Suc. 4, 1900 La Plata, Argentina 
690 1 0 |a ALKALOID 
690 1 0 |a PIPERIDINE DERIVATIVE 
690 1 0 |a TERPENOID 
690 1 0 |a ARTICLE 
690 1 0 |a DRUG SYNTHESIS 
690 1 0 |a REACTION ANALYSIS 
700 1 |a Baldessari, A. 
700 1 |a Ponce, M.A. 
700 1 |a Rodriguez, J.B. 
700 1 |a Gros, E.G. 
700 1 |a Caram, J.A. 
700 1 |a Marschoff, C.M. 
773 0 |d 1994  |g v. 35  |h pp. 6967-6970  |k n. 38  |p Tetrahedron Lett.  |x 00404039  |w (AR-BaUEN)CENRE-415  |t Tetrahedron Letters 
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856 4 0 |u https://doi.org/10.1016/0040-4039(94)88200-2  |y DOI 
856 4 0 |u https://hdl.handle.net/20.500.12110/paper_00404039_v35_n38_p6967_Samaniego  |y Handle 
856 4 0 |u https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404039_v35_n38_p6967_Samaniego  |y Registro en la Biblioteca Digital 
961 |a paper_00404039_v35_n38_p6967_Samaniego  |b paper  |c PE 
962 |a info:eu-repo/semantics/article  |a info:ar-repo/semantics/artículo  |b info:eu-repo/semantics/publishedVersion 
963 |a VARI 
999 |c 80019 

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