Synthesis of 2,7-Diazabicyclo[3.3.0]octane and 2,7-Diazabicyclo[3.3.0]oct-4-ene Derivatives via Cyclization Reaction and Julia Reaction

References and Notes

• Massiot , G. and Delaude , C. 1986 . The Alkaloids , Edited by: Manske , R. H. F. Vol. 27 , New York : Academic Press, Inc. . Chapter 3
   Google Scholar
• Padwa , A. and Norman , B. H. 1990 . J. Org. Chem. , 55 : 4081
   Google Scholar
• Wang , C. J. and Wuonola , M. A. 1990 . Org. Prep. Rep. , : 447
   Google Scholar
• Domagala , J. M. 1994 . J. Antimicrob. Chemother. , 33 : 685
   PubMed Web of Science ®Google Scholar
• Braish , T. B. and Fox , D. E. 1990 . J. Org. Chem. , 55 : 1684
   Web of Science ®Google Scholar
• Jordis , U. , Sauter , F. , Siddigi , S. M. , Kuenberg , B. and Bhattacharya , K. 1990 . Synthesis , : 925
   Google Scholar
• Gubert , S. , Broaojos , C. , Sacristan , A. and Ortiz , J. A. 1991 . Synthesis , : 318
   Google Scholar
• Lee , J. W. , Son , H. J. , Lee , J. H. , Jung , E. Y. , Yoon , G. J. and Park , M. H. in press . Synth. Commun. ,
   Google Scholar
• Lee , J. W. , Son , H. J. and Choi , M. J. 1994 . Korean J. Med. Chem. , 4 : 119
   Google Scholar
• Padwa , A. and Norman , B. H. 1990 . J. Org. Chem. , 55 : 4801 cf. N-Alkylated 3-phenysulfonyl-3-pyrroline have been obtained by the reaction of amines with 2,3-bis(phenylsulfonyl)-1,3-butadiene, followed by elimination step, see
   Google Scholar
• Julia , M. , Launay , M. , Stacino , J. P. and Verpeaux , J. N. 1982 . Tetrahedron Lett. , 23 : 2465
   Web of Science ®Google Scholar
• Van Dort , P. C. and Fuchs , P. L. 1994 . J. Am. Chem. Soc. , 116 : 5657 For the cyclized β-hydroxy sulfone, see:, The generation of double bond was derived from the mesylation of β-hydroxy sulfone and in situ β-elimination by excess Et3N. Preparation of vinyl sulfone from β-hydroxy sulfone in 2 steps, see
   Google Scholar
• McDowell , S. T. and Stirling , C. J. M. 1967 . J. Chem. Soc. (B) , : 351
   Google Scholar
• We gratefully thank Prof. Kim, M. J. for X-ray crystallographic analysis
   Google Scholar
• We have found that the intramolecular cyclization reaction of sulfone ester have been influenced on the protecting group of nitrogen at 4-position of pyrrolidine. Studies on the cyclization reaction according to nitrogen protecting group and electron withdrawing group are underway and will be reported in due course
   Google Scholar
• Grimm , E. L. , Coutu , M. L. and Trimble , L. A. 1993 . Tetrahedron Lett. , 34 : 7017 and references therein
   Web of Science ®Google Scholar
• Grimm , E. L. , Levac , S. and Coutu , M. L. 1994 . Tetrahedron Lett. , 35 : 5369
   Google Scholar
• Grimm , E. L. , Levac , S. and Trimble , L. A. 1994 . s Tetrahedron Lett. , 35 : 6847
   Web of Science ®Google Scholar
• Julia , M. and Paris , J. M. 1973 . Tetrahedron Lett. , : 4833
   Web of Science ®Google Scholar
• Kende , A. S. and Mendoza , J. S. 1990 . Tetrahedron Lett. , 31 : 7105
   Google Scholar
• Ihara , M. , Suzuki , S. , Taniguchi , T. , Tokunaga , Y. and Fukumoto , K. 1994 . Synlett , : 859
   Google Scholar
• Simpkins , N. S. 1993 . Sulphones in Organic Synthesis , New York : Pergamon Press .
   Google Scholar
• Ku , Y. Y. , Patel , R. R. , Roden , B. A. and Sawick , D. P. 1994 . Tetrahedron Lett. , 35 : 6017 Removal of the sulfonyl group, see, and references therein
   Web of Science ®Google Scholar
• Lee , G. H. , Choi , E. B. , Lee , E. and Pak , C. S. 1993 . Tetrahedron Lett. , 34 : 4541
   Web of Science ®Google Scholar
• 1: mp 140∼142°C; 1Hnmr (80 MHz, CDCl3) δ 1.45(s, 9H), 1.47(s, 9H), 2.26(br, 1H), 2.75∼3.02(m, 1H), 3.17∼3.33(m, 1H), 3.44∼3.76(m, 5H), 4.17(m, 1H), 4.38(m, 1H). 2: mp 96∼100°C; 1Hnmr (80 MHz, CDCl3) δ 1.47(s, 18H), 2.87(dd, J=9.87 Hz; J=8.72 Hz, 1H), 3.89(br, 2H), 4.11(m, 1H), 4.34(br, 2H), 4.67(m, 1H), 5.61(br, 1H); ir(ν, cm−1) 1106, 1129, 1152, 1174, 1333, 1365, 1402, 1477, 1676, 1697, 2876, 2978; ms(m/z) 57(100), 80(73.2), 153(39.9), 197(42.8), 253(M+ - 57, loss of t-Bu, 5.1). 9: mp 174∼176°C; 1Hnmr (80 MHz, CDCl3) δ 1.41(s, 9H), 1.48(s, 9H), 3.12∼4.22(m. 7H), 4.94(m, 1H), 7.53∼7.75(m, 3H), 7.98∼8.10(m, 2H); ir(ν, cm−1) 1149, 1169, 1251, 1308, 1368, 1408, 1680, 1697, 3399
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