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Volumn 74, Issue 7, 2009, Pages 2832-2836

One-carbon ring expansion of azetidines via ammonium ylide [1,2]-shifts: A simple route to substituted pyrrolidines

Author keywords

[No Author keywords available]

Indexed keywords

AZETIDINE; AZETIDINES; CARBON RINGS; CARBONYL GROUPS; EXOCYCLIC GROUPS; PYRROLIDINES; RING EXPANSIONS; STABILIZING GROUPS;

EID: 64249127625     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9001323     Document Type: Article
Times cited : (55)

References (59)
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    • For other examples of azetidinium ylide ring expansions, see:a
    • For other examples of azetidinium ylide ring expansions, see:(a) Couty, F.; Durrat, F.; Evano, G.; Marrot, J. Eur. J. Org. Chem. 2006, 4214-4223.
    • (2006) Eur. J. Org. Chem , pp. 4214-4223
    • Couty, F.1    Durrat, F.2    Evano, G.3    Marrot, J.4
  • 24
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    • The known azetidine substrates 1a,b,d,e were prepared via the following literature procedures: (a) 1a: Rodebaugh, R. M.; Cromwell, N. H. J. Heterocycl. Chem. 1968, 5, 309-311.
    • The known azetidine substrates 1a,b,d,e were prepared via the following literature procedures: (a) 1a: Rodebaugh, R. M.; Cromwell, N. H. J. Heterocycl. Chem. 1968, 5, 309-311.
  • 25
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    • 1b : Wasserman, H. H.; Lipshutz, B. H.; Tremper, A. W.; Wu, S. W. J. Org. Chem. 1981, 46, 2991-2999.
    • (b) 1b : Wasserman, H. H.; Lipshutz, B. H.; Tremper, A. W.; Wu, S. W. J. Org. Chem. 1981, 46, 2991-2999.
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    • 1d : Leonard, N. J.; Durand, D. A. J. Org. Chem. 1968, 33, 1322-1333.
    • (c) 1d : Leonard, N. J.; Durand, D. A. J. Org. Chem. 1968, 33, 1322-1333.
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    • 1e: Lai, G. Synth. Commun. 2001, 31, 565-568.
    • (d) 1e: Lai, G. Synth. Commun. 2001, 31, 565-568.
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    • Methyl N-allylazetidine-2-carboxylate 1c was prepared using method B from ref 11b.
    • (e) Methyl N-allylazetidine-2-carboxylate 1c was prepared using method B from ref 11b.
  • 30
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    • Ethyl diazoacetate 2a was purchased from Sigma-Aldrich.
    • (a) Ethyl diazoacetate 2a was purchased from Sigma-Aldrich.
  • 31
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    • Diethyl diazomalonate 2b was prepared via the standard diazotransfer procedure described in: Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; Wiley-Interscience: New York, 1998; p 10.
    • (b) Diethyl diazomalonate 2b was prepared via the standard diazotransfer procedure described in: Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; Wiley-Interscience: New York, 1998; p 10.
  • 32
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    • Diazoacetophenone 2c : Jung, M. E.; Min, S.; Houk, K. N.; Ess, D. J. Org. Chem. 2004, 69, 9085-9089.
    • (c) Diazoacetophenone 2c : Jung, M. E.; Min, S.; Houk, K. N.; Ess, D. J. Org. Chem. 2004, 69, 9085-9089.
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    • 2-Diazo-3-oxo-3-phenylpropionic acid ethyl ester 2d: Lall, M. S.; Ramtohul, Y. K.; James, M. N. G.; Vederas, J. C. J. Org. Chem. 2002, 67, 1536-1547.
    • (d) 2-Diazo-3-oxo-3-phenylpropionic acid ethyl ester 2d: Lall, M. S.; Ramtohul, Y. K.; James, M. N. G.; Vederas, J. C. J. Org. Chem. 2002, 67, 1536-1547.
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    • Carboxyproline derivatives are of interest as rigid aspartate analogues: (a) Flamant-Robin, C.; Wang, Q.; Chiaroni, A.; Sasaki, N. A. Tetrahedron 2002, 58, 10475-10484.
    • Carboxyproline derivatives are of interest as rigid aspartate analogues: (a) Flamant-Robin, C.; Wang, Q.; Chiaroni, A.; Sasaki, N. A. Tetrahedron 2002, 58, 10475-10484.
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    • Khlebnikov and co-workers observed a similar oxidative process upon heating a polycyclic 3-carboxyproline diester with ethyl diazoacetate in the presence of copper powder. The mechanism of this transformation is unclear and under current studv. Khlebnikov, A. F.; Novikov. M. S.; Kostikov, R. R.; Kopf, J. Russ. J. Org. Cem. 2005, 41, 1341-1348.
    • Khlebnikov and co-workers observed a similar oxidative process upon heating a polycyclic 3-carboxyproline diester with ethyl diazoacetate in the presence of copper powder. The mechanism of this transformation is unclear and under current studv. Khlebnikov, A. F.; Novikov. M. S.; Kostikov, R. R.; Kopf, J. Russ. J. Org. Cem. 2005, 41, 1341-1348.
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    • Facile aerobic debenzoylative oxidation of α-aminoketones under basic conditions has been observed by Garcia-Valverde and co-workers: GarcíaValverde, M, Pedrosa, R, Vicente' M. Synlett 2002, 2092-2093
    • (a) Facile aerobic debenzoylative oxidation of α-aminoketones under basic conditions has been observed by Garcia-Valverde and co-workers: GarcíaValverde, M.; Pedrosa, R.; Vicente' M. Synlett 2002, 2092-2093.
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    • For a related oxidative deacylation, see
    • (b) For a related oxidative deacylation, see: Yijima. C.; Hino, F.; Suda, K. Synthesis 1981, 610-611.
    • (1981) Synthesis , pp. 610-611
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    • Epimerization of one or both stereocenters may also occur during the reaction. However, since the diastereomeric mixtures were inseparable, it was not possible to probe for this by resubjecting pure diastereomers to the reaction conditions
    • Epimerization of one or both stereocenters may also occur during the reaction. However, since the diastereomeric mixtures were inseparable, it was not possible to probe for this by resubjecting pure diastereomers to the reaction conditions.
  • 55
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    • For the role of transition metal catalysts in periselectivity, see
    • (c) For the role of transition metal catalysts in periselectivity, see: Marmsäter, F. P.; Vanecko, J. A.; West, F. G. Org. Lett. 2004, 6, 1657-1660.
    • (2004) Org. Lett , vol.6 , pp. 1657-1660
    • Marmsäter, F.P.1    Vanecko, J.A.2    West, F.G.3
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    • None of the 3,3-dimethyl-2-pyrrolidinone product analogous to 7 was isolated from reaction of 1d with 2c.
    • None of the 3,3-dimethyl-2-pyrrolidinone product analogous to 7 was isolated from reaction of 1d with 2c.
  • 59
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    • For a related example of exclusive benzyl migration rather than ring expansion of an azetidinium ylide stabilized by ester and trifluoromethyl groups, see: Osipov, S. N, Sewald, N, Kolomiets, A. F, Fokin, A. V, Burger, K. Tetrahedron Lett. 1996, 37, 615-618
    • For a related example of exclusive benzyl migration rather than ring expansion of an azetidinium ylide stabilized by ester and trifluoromethyl groups, see: Osipov, S. N.; Sewald, N.; Kolomiets, A. F.; Fokin, A. V.; Burger, K. Tetrahedron Lett. 1996, 37, 615-618.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.