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Volumn 8, Issue 24, 2006, Pages 5521-5524

Synthesis of β,γ-unsaturated lactams via a magnesium iodide promoted ring expansion of secondary methylenecyclopropyl amides

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; CYCLOPROPANE DERIVATIVE; IODIDE; LACTAM; MAGNESIUM DERIVATIVE; MAGNESIUM IODIDE; UNCLASSIFIED DRUG;

EID: 33845972255     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0621957     Document Type: Article
Times cited : (36)

References (55)
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  • 2
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    • For a recent review of MCPs used for the preparation of heterocyclic compounds, see
    • For a recent review of MCPs used for the preparation of heterocyclic compounds, see: Brandi, A.; Cicchi, S.; Cordero, F. M.; Goti, A. Chem. Rev. 2003, 103, 1213.
    • (2003) Chem. Rev , vol.103 , pp. 1213
    • Brandi, A.1    Cicchi, S.2    Cordero, F.M.3    Goti, A.4
  • 3
    • 33745042632 scopus 로고    scopus 로고
    • For recent selected references on the synthetic utility of MCPs. see: a
    • For recent selected references on the synthetic utility of MCPs. see: (a) Shi, M.; Liu, L.-P.; Tang, J. J. Am. Chem. Soc. 2006, 128, 7430.
    • (2006) J. Am. Chem. Soc , vol.128 , pp. 7430
    • Shi, M.1    Liu, L.-P.2    Tang, J.3
  • 15
    • 0037024163 scopus 로고    scopus 로고
    • For our contributions to this area, see: a
    • For our contributions to this area, see: (a) Lautens, M.; Han, W. J. Am. Chem. Soc. 2002, 124, 6312.
    • (2002) J. Am. Chem. Soc , vol.124 , pp. 6312
    • Lautens, M.1    Han, W.2
  • 19
    • 33845993382 scopus 로고    scopus 로고
    • Single point calculations using Spartan at the RB3LYP level show an energy difference of 17.7 kcal/mol between the more stable endo product 3g and the less stable exo product 2g.
    • Single point calculations using Spartan at the RB3LYP level show an energy difference of 17.7 kcal/mol between the more stable endo product 3g and the less stable exo product 2g.
  • 38
    • 33845973115 scopus 로고
    • U.S. Patent 3,984,559
    • (d) Weinstock, J. U.S. Patent 3,984,559, 1976.
    • (1976)
    • Weinstock, J.1
  • 41
    • 33846032062 scopus 로고    scopus 로고
    • See Supporting Information for details
    • See Supporting Information for details.
  • 42
    • 33845977839 scopus 로고    scopus 로고
    • N′ reaction of allylic iodides, see: McDowell, C. A.; Lossing, F. P.; Henderson, I. H. S.; Farmer, J. B. Can. J. Chem. 1956, 34, 345.
    • N′ reaction of allylic iodides, see: McDowell, C. A.; Lossing, F. P.; Henderson, I. H. S.; Farmer, J. B. Can. J. Chem. 1956, 34, 345.
  • 43
    • 33947448784 scopus 로고    scopus 로고
    • Although the major route of isomerization is likely via Su2' attack of iodide, there is a possibility that trace !2, either generated in situ or as an impurity in the commercial MgI2, could lead to allylic iodide isomerization. For instance, see: (a) Sibbett, D. J, Noyes, R. M. J. Am. Chem. Soc. 1953, 75, 761
    • 2, could lead to allylic iodide isomerization. For instance, see: (a) Sibbett, D. J.; Noyes, R. M. J. Am. Chem. Soc. 1953, 75, 761.
  • 46
    • 33751554315 scopus 로고    scopus 로고
    • Although an SN2′ ring-closing pathway (5-endo-trig) is unfavored by Balwin's rules, similar 5-endo-trig ring-closing reactions have been reported for the synthesis of pyrrolidines. See, for example: (a) Padwa, A, Norman, B. H. J. Org. Chem. 1990, 55, 4801
    • N2′ ring-closing pathway (5-endo-trig) is unfavored by Balwin's rules, similar 5-endo-trig ring-closing reactions have been reported for the synthesis of pyrrolidines. See, for example: (a) Padwa, A.; Norman, B. H. J. Org. Chem. 1990, 55, 4801.
  • 53
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    • 1 H NMR analysis showed only 2k along with unreacted starting material. Extensive formation of the endo isomer (3k) along with significant amounts of decomposition were observed after prolonged heating.
    • 1 H NMR analysis showed only 2k along with unreacted starting material. Extensive formation of the endo isomer (3k) along with significant amounts of decomposition were observed after prolonged heating.
  • 54
    • 33846004930 scopus 로고    scopus 로고
    • 2O are used to reverse this selectivity. See, for example: (a) Ferrer. M.; Sànchez-Baeza, F.; Messeguer, A.; Diez, A.; Rubiralta, M. J. Chem. Soc. Chem. Commun. 1995, 293.
    • 2O are used to reverse this selectivity. See, for example: (a) Ferrer. M.; Sànchez-Baeza, F.; Messeguer, A.; Diez, A.; Rubiralta, M. J. Chem. Soc. Chem. Commun. 1995, 293.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.