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Volumn 87, Issue 8, 2009, Pages 1117-1121

Synthesis of both isomers of aziridine derived from the mixture of cis- And trans-limonene oxide

Author keywords

amino alcohol; Cis And trans limonene oxide; Limonene aziridine; O tosylation

Indexed keywords

AZIRIDINES; CHIRAL BUILDING BLOCKS; CIS- AND TRANS-LIMONENE OXIDE; LIMONENE AZIRIDINE; LIMONENE OXIDE; MULTI-GRAM QUANTITIES; O-TOSYLATION; SCALE-UP;

EID: 69349096374     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/V09-085     Document Type: Article
Times cited : (5)

References (56)
  • 1
    • 0015511562 scopus 로고
    • For examples of synthesis, utilizing limonene as the chiral template
    • Van Tamelen, E. E.; Anderson, R. J doi:10.1021/ja00778a047. PMID:5079966
    • (a) For examples of synthesis, utilizing limonene as the chiral template, see: Van Tamelen, E. E.; Anderson, R. J. J. Am. Chem. Soc. 1972, 94 (23), 8225-8228. doi:10.1021/ja00778a047. PMID:5079966.;
    • (1972) J. Am. Chem. Soc , vol.94 , Issue.23 , pp. 8225-8228
  • 3
    • 41849140432 scopus 로고
    • doi:10.1016/S0040-4020(01)80068-5
    • Baudouy, R.; Prince, P. Tetrahedron 1989, 45 (7), 2067-2074. doi:10.1016/S0040-4020(01)80068-5.;
    • (1989) Tetrahedron , vol.45 , Issue.7 , pp. 2067-2074
    • Baudouy, R.1    Prince, P.2
  • 4
    • 0042969835 scopus 로고
    • doi:10.1021/ja00007a039
    • Paquette, L. A.; Kang, H.-J. J. Am. Chem. Soc. 1991, 113 (7), 2610-2621. doi:10.1021/ja00007a039.;
    • (1991) J. Am. Chem. Soc , vol.113 , Issue.7 , pp. 2610-2621
    • Paquette, L.A.1    Kang, H.-J.2
  • 5
    • 0001617409 scopus 로고
    • doi:10.10.16/S0040-4039(00)84154-4
    • (e) Mori, K.; Kato, M. Tetrahedron Lett. 1986, 27 (8), 981-982. doi:10.10.16/S0040-4039(00)84154-4.;
    • (1986) Tetrahedron Lett , vol.27 , Issue.8 , pp. 981-982
    • Mori, K.1    Kato, M.2
  • 6
    • 84988126991 scopus 로고
    • doi:10.1055/s-1989-27309
    • (f) Marron, B. E.; Nicolaou, K. C. Synthesis 1989, 1989 (07), 537-539. doi:10.1055/s-1989-27309.;
    • (1989) Synthesis , vol.1989 , Issue.7 , pp. 537-539
    • Marron, B.E.1    Nicolaou, K.C.2
  • 7
    • 0005837752 scopus 로고
    • doi:10.1080/00397918808068256
    • (g) Tius, M. A.; Kerr, M. A. Synth. Commun. 1988, 18 (16), 1905-1911. doi:10.1080/00397918808068256.;
    • (1988) Synth. Commun , vol.18 , Issue.16 , pp. 1905-1911
    • Tius, M.A.1    Kerr, M.A.2
  • 8
    • 0007912569 scopus 로고
    • doi:10.1055/s-1979-28835
    • (h) Dauphin, G. Synthesis 1979, 1979 (10), 799-801. doi:10.1055/s-1979- 28835.;
    • (1979) Synthesis , vol.1979 , Issue.10 , pp. 799-801
    • Dauphin, G.1
  • 10
    • 0025364933 scopus 로고
    • doi:10.1016/00404039(90)80114-2
    • (j) Wender, P. A.; Singh, S. K. Tetrahedron Lett. 1990, 31 (18), 2517-2520. doi:10.1016/00404039(90)80114-2.;
    • (1990) Tetrahedron Lett , vol.31 , Issue.18 , pp. 2517-2520
    • Wender, P.A.1    Singh, S.K.2
  • 16
    • 0029061840 scopus 로고
    • doi:10.1016/00404020(95)00447-G
    • (b) Masui, M.; Shioiri, T. Tetrahedron 1995, 51 (30), 8363-8370. doi:10.1016/00404020(95)00447-G.;
    • (1995) Tetrahedron , vol.51 , Issue.30 , pp. 8363-8370
    • Masui, M.1    Shioiri, T.2
  • 20
    • 37249059525 scopus 로고    scopus 로고
    • doi:10.1016/j.tet.2007.07.065
    • (f) Szakonyi, Z.; Hetenyi, A.; Fulop, F. Tetrahedron 2008, 64 (6), 1034-1039. doi:10.1016/j.tet.2007.07.065.
    • (2008) Tetrahedron , vol.64 , Issue.6 , pp. 1034-1039
    • Szakonyi, Z.1    Hetenyi, A.2    Fulop, F.3
  • 22
    • 0036374173 scopus 로고    scopus 로고
    • For recent reviews on aziridines, including their synthesis in optically active form and their ring-opening reactions
    • Sweeney, J. B doi:10.1039/b0060151. PMID: 12357722
    • (a) For recent reviews on aziridines, including their synthesis in optically active form and their ring-opening reactions, see: Sweeney, J. B. Chem. Soc. Rev. 2002, 31 (5), 247-258. doi:10.1039/b0060151. PMID: 12357722.;
    • (2002) Chem. Soc. Rev , vol.31 , Issue.5 , pp. 247-258
  • 23
    • 0033800394 scopus 로고    scopus 로고
    • doi:10.1055/s2000-7097
    • (b) McCoull, W.; Davis, F. A. Synthesis 2000, 2000 (10), 1347-1365. doi:10.1055/s2000-7097.;
    • (2000) Synthesis , vol.2000 , Issue.10 , pp. 1347-1365
    • McCoull, W.1    Davis, F.A.2
  • 24
    • 0033524716 scopus 로고    scopus 로고
    • doi:10.1016/S0040-4020(98)01199-5
    • Atkinson, R. S. Tetrahedron 1999, 55 (6), 1519-1559. doi:10.1016/S0040- 4020(98)01199-5.;
    • (1999) Tetrahedron , vol.55 , Issue.6 , pp. 1519-1559
    • Atkinson, R.S.1
  • 26
    • 0030907093 scopus 로고    scopus 로고
    • doi:10.1016/S0957-4166(97)00177-8
    • (e) Osborn, H. M. I.; Sweeney, J. B. Tetrahedron Asymmetry 1997, 8(11), 16931715. doi:10.1016/S0957-4166(97)00177-8.;
    • (1997) Tetrahedron Asymmetry , vol.8 , Issue.11 , pp. 16931715
    • Osborn, H.M.I.1    Sweeney, J.B.2
  • 27
    • 33748605775 scopus 로고
    • doi:10.1002/anie.199405991
    • (f) Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33 (6), 599-619. doi:10.1002/anie.199405991.;
    • (1994) Angew. Chem., Int. Ed. Engl , vol.33 , Issue.6 , pp. 599-619
    • Tanner, D.1
  • 28
    • 0642377196 scopus 로고
    • doi:10.1351/pac199365061319
    • (g) Tanner, D. Pure Appl. Chem. 1993, 65 (6), 1319-1328. doi:10.1351/pac199365061319.
    • (1993) Pure Appl. Chem , vol.65 , Issue.6 , pp. 1319-1328
    • Tanner, D.1
  • 29
    • 0002215335 scopus 로고
    • For examples of ring closure of amino alcohols and their derivatives
    • Kelly, J. W.; Eskew, N. L.; Evans, S. A. doi:10.1021/jo00351a020
    • (a) For examples of ring closure of amino alcohols and their derivatives, see: Kelly, J. W.; Eskew, N. L.; Evans, S. A. J. Org. Chem. 1986, 51 (1), 95-97. doi:10.1021/jo00351a020.;
    • (1986) J. Org. Chem , vol.51 , Issue.1 , pp. 95-97
  • 32
    • 33644993161 scopus 로고    scopus 로고
    • doi:10.1016/j.tet.2006.02.003
    • Song, L.; Servajean, V.; Thierry, J. Tetrahedron 2006, 62 (15), 3509-3516. doi:10.1016/j.tet.2006.02.003.
    • (2006) Tetrahedron , vol.62 , Issue.15 , pp. 3509-3516
    • Song, L.1    Servajean, V.2    Thierry, J.3
  • 33
    • 33845282537 scopus 로고
    • An exception to this would be to utilize proline as the amino acid, and derivatives of this important synthon have been widely used as chiral auxilaries. for example
    • Soai, K.; Okawa, A.; Tatsuya, K.; Ogawa, K. J doi:10.1021/ja00257a034
    • (a) An exception to this would be to utilize proline as the amino acid, and derivatives of this important synthon have been widely used as chiral auxilaries. For example, see: Soai, K.; Okawa, A.; Tatsuya, K.; Ogawa, K. J. Am. Chem. Soc. 1.987, 109 (23), 7111-7115. doi:10.1021/ja00257a034.;
    • (1987) Am. Chem. Soc , vol.109 , Issue.23 , pp. 7111-7115
  • 34
    • 27644528135 scopus 로고    scopus 로고
    • doi:10.1016/j.tetlet.2005.09.172
    • (b) KrzemMski, M. P.; Wojtczak, A. Tetrahedron Lett. 2005, 46 (48), 8299-8302. doi:10.1016/j.tetlet.2005.09.172.;
    • (2005) Tetrahedron Lett , vol.46 , Issue.48 , pp. 8299-8302
    • Krzemmski, M.P.1    Wojtczak, A.2
  • 36
    • 0000096835 scopus 로고    scopus 로고
    • For a review on clickchem
    • Kolb, H. C.; Finn, M. G.; Sharpless, K. B doi:10.1002/1521-3773(20010601) 40:11<2004::AIDANIE2004>3.0.CO;2-5
    • (a) For a review on ClickChem, see: Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40 (11), 2004-2021. doi:10.1002/1521- 3773(20010601)40:11<2004::AIDANIE2004>3.0.CO;2-5.;
    • (2001) Angew. Chem., Int. Ed , vol.40 , Issue.11 , pp. 2004-2021
  • 38
    • 0037428006 scopus 로고    scopus 로고
    • doi:10.1021/jo026506c. PMID: 12515464
    • (a) For examples, see: Davis, C. E.; Bailey, J. L.; Lockner, J. W.; Coates, R. M. J. Org. Chem. 2003, 68 (1), 75-82. doi:10.1021/jo026506c. PMID: 12515464.;
    • (2003) Org. Chem , vol.68 , Issue.1 , pp. 75-82
    • Davis, C.E.1    Bailey, J.L.2    Lockner, J.W.3    Coates, R.M.J.4
  • 40
    • 0013473360 scopus 로고
    • doi:10.1021/jo00277a037
    • Subbaraj, A.; Rao, O. S.; Lwowski, W. J. Org. Chem. 1989, 54 (16), 3945-3952. doi:10.1021/jo00277a037.;
    • (1989) J. Org. Chem , vol.54 , Issue.16 , pp. 3945-3952
    • Subbaraj, A.1    Rao, O.S.2    Lwowski, W.3
  • 41
    • 0033588056 scopus 로고    scopus 로고
    • doi:10.1016/S0040-4039(99)01210-1
    • Bergmeier, S. C; Seth, P. P. Tetrahedron Lett. 1999, 40 (34), 6181-6184. doi:10.1016/S0040-4039(99)01210-1.;
    • (1999) Tetrahedron Lett , vol.40 , Issue.34 , pp. 6181-6184
    • Bergmeier, S.C.1    Seth, P.P.2
  • 42
    • 0001150457 scopus 로고
    • doi:10.1080/00397918808077348
    • (e) Parrish, E.; Nes, W. D. Synth. Commun. 1988, 18 (2), 221-226. doi:10.1080/00397918808077348.;
    • (1988) Synth. Commun , vol.18 , Issue.2 , pp. 221-226
    • Parrish, E.1    Nes, W.D.2
  • 44
    • 0000912147 scopus 로고
    • Fractional distillation is possible but extremely inefficient
    • doi:10.1021/jo01344a062Royals, E. E.; Leffingwell, J. C. J
    • Fractional distillation is possible but extremely inefficient: Royals, E. E.; Leffingwell, J. C. J. Org. Chem. 1966, 31 (6), 1937-1944. doi:10.1021/jo01344a062.
    • (1966) Org. Chem , vol.31 , Issue.6 , pp. 1937-1944
  • 48
    • 37049089053 scopus 로고
    • Under harsh conditions, both epoxides can be opened with dimethylamine, and the corresponding amino alcohols can be separated by salt formation and crystallization. for examples of this and the susbsequent conversion of the amino alcohols back to the diastereomerically pure epoxides
    • Baker, R.; Borges, M.; Cooke, N. G.; Herbert, R. H. doi:10.1039/ C39870000414
    • (a) Under harsh conditions, both epoxides can be opened with dimethylamine, and the corresponding amino alcohols can be separated by salt formation and crystallization. For examples of this and the susbsequent conversion of the amino alcohols back to the diastereomerically pure epoxides, see: Baker, R.; Borges, M.; Cooke, N. G.; Herbert, R. H. J. Chem. Soc., Chem. Commun. 1987, (6): 414. doi:10.1039/C39870000414.;
    • (1987) J. Chem. Soc., Chem. Commun , vol.6 , pp. 414
  • 49
    • 0000164440 scopus 로고
    • doi:10.1021/jo01024a042
    • (b) Newhall, W. F. J. Org. Chem. 1964, 29 (1), 185-187. doi:10.1021/jo01024a042.
    • (1964) J. Org. Chem , vol.29 , Issue.1 , pp. 185-187
    • Newhall, W.F.1
  • 54
    • 0031579475 scopus 로고    scopus 로고
    • Enzyme-mediated hydrolysis has been reported
    • Weijers, C. A. G. M doi:10.1016/S0957-4166(97)00012-8
    • (a) Enzyme-mediated hydrolysis has been reported, see: Weijers, C. A. G. M. Tetrahedron Asymmetry 1997, 8 (4), 639-647. doi:10.1016/S0957-4166(97)00012- 8.;
    • (1997) Tetrahedron Asymmetry , vol.8 , Issue.4 , pp. 639-647


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.