메뉴 건너뛰기




Volumn 17, Issue 12, 2012, Pages 14249-14259

Recent developments in the reformatsky-claisen rearrangement

Author keywords

Claisen rearrangement; Indium; Reformatsky reaction; Reformatsky Claisen rearrangement; Zinc

Indexed keywords

ACETIC ACID DERIVATIVE; ALLYL COMPOUND; BIOLOGICAL PRODUCT; BROMOACETIC ACID; ZINC;

EID: 84871564870     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules171214249     Document Type: Review
Times cited : (12)

References (31)
  • 1
    • 0003073955 scopus 로고
    • Stereo and regiochemistry of the claisen rearrangement: Applications to natural products synthesis
    • Ziegler, F.E. Stereo- and regiochemistry of the Claisen rearrangement: Applications to natural products synthesis. Acc. Chem. Res. 1977, 10, 227-232.
    • (1977) Acc. Chem. Res. , vol.10 , pp. 227-232
    • Ziegler, F.E.1
  • 2
    • 0008810969 scopus 로고
    • Natural products synthesis starting with carbohydrates based on the claisen rearrangement protocol
    • Atta-Ur-Rahman, Ed.; Elsevier: Amsterdam, The Netherlands
    • Tadano, K.-I. Natural products synthesis starting with carbohydrates based on the Claisen rearrangement protocol. In Studies in Natural Products Chemistry: Stereoselective Synthesis (Part F); Atta-Ur-Rahman, Ed.; Elsevier: Amsterdam, The Netherlands, 1992; Volume 10, pp. 405-455.
    • (1992) Studies in Natural Products Chemistry: Stereoselective Synthesis (Part F) , vol.10 , pp. 405-455
    • Tadano, K.-I.1
  • 3
    • 70350519149 scopus 로고    scopus 로고
    • [3,3]-Sigmatropic rearrangements Recent applications in the total synthesis of natural products
    • Ilardi, E.A.; Stivala, C.E.; Zakarian, A. [3,3]-Sigmatropic rearrangements: Recent applications in the total synthesis of natural products. Chem. Soc. Rev. 2009, 38, 3133-3148.
    • (2009) Chem Soc Rev , vol.38 , pp. 3133-3148
    • Ilardi, E.A.1    Stivala, C.E.2    Zakarian, A.3
  • 4
    • 79960983511 scopus 로고    scopus 로고
    • A synergistic approach to polycyclics via a strategic utilization of claisen rearrangement and olefin metathesis
    • Kotha, S.; Krishna, N.G.; Halder, S.; Misra, S. A synergistic approach to polycyclics via a strategic utilization of Claisen rearrangement and olefin metathesis. Org. Biomol. Chem. 2011, 9, 5597-5624.
    • (2011) Org. Biomol. Chem. , vol.9 , pp. 5597-5624
    • Kotha, S.1    Krishna, N.G.2    Halder, S.3    Misra, S.4
  • 6
    • 85066103748 scopus 로고
    • The claisen rearrangement in organic synthesis: 1967 to january 1977
    • Bennett, G.B. The Claisen rearrangement in organic synthesis: 1967 to January 1977. Synthesis 1977, 589-606.
    • (1977) Synthesis , pp. 589-606
    • Bennett, G.B.1
  • 7
    • 85082586002 scopus 로고
    • The hetero-cope rearrangement in organic synthesis
    • Blechert, S. The hetero-Cope rearrangement in organic synthesis. Synthesis 1989, 71-82.
    • (1989) Synthesis , pp. 71-82
    • Blechert, S.1
  • 8
    • 0000217402 scopus 로고
    • Claisen rearrangements
    • Trost, B.M., Ed.; Pergamon Press: Oxford, UK
    • Wipf, P. Claisen rearrangements. In Comprehensive Organic synthesis; Trost, B.M., Ed.; Pergamon Press: Oxford, UK, 1991; Volume 5, pp. 827-873.
    • (1991) Comprehensive Organic synthesis , vol.5 , pp. 827-873
    • Wipf, P.1
  • 9
    • 4344610661 scopus 로고    scopus 로고
    • Claisen rearrangement over the past nine decades
    • Martin Castro, A.M. Claisen rearrangement over the past nine decades. Chem. Rev. 2004, 104, 2939.
    • (2004) Chem. Rev. , vol.104 , pp. 2939
    • Martin Castro, A.M.1
  • 10
    • 0000295477 scopus 로고
    • Claisen rearrangement of allyl esters
    • Ireland, R.E.; Mueller, R.H. Claisen rearrangement of allyl esters. J. Am. Chem. Soc. 1972, 94, 5897-5898.
    • (1972) J. Am. Chem. Soc. , vol.94 , pp. 5897-5898
    • Ireland, R.E.1    Mueller, R.H.2
  • 11
    • 33847799798 scopus 로고
    • The ester enolate claisen rearrangement. Stereochemical control through stereoselective enolate formation
    • Ireland, R.E.; Mueller, R.H.; Willard, A.K. The ester enolate Claisen rearrangement. Stereochemical control through stereoselective enolate formation. J. Am. Chem. Soc. 1976, 98, 2868-2877.
    • (1976) J. Am. Chem. Soc. , vol.98 , pp. 2868-2877
    • Ireland, R.E.1    Mueller, R.H.2    Willard, A.K.3
  • 12
    • 33751499786 scopus 로고
    • Stereochemical control in the ester enolate claisen rearrangement. 1. Stereoselectivity in silyl ketene acetal formation
    • Ireland, R.E.; Wipf, P.; Armstrong, J.D. Stereochemical control in the ester enolate Claisen rearrangement. 1. Stereoselectivity in silyl ketene acetal formation. J. Org. Chem. 1991, 56, 650-657.
    • (1991) J. Org. Chem. , vol.56 , pp. 650-657
    • Ireland, R.E.1    Wipf, P.2    Armstrong, J.D.3
  • 13
    • 0000964816 scopus 로고
    • Stereochemical control in the ester enolate claisen rearrangement. 2. Chairlike vs boatlike transition-state selection
    • Ireland, R.E.; Wipf, P.; Xiang, J.-N. Stereochemical control in the ester enolate Claisen rearrangement. 2. Chairlike vs boatlike transition-state selection. J. Org. Chem. 1991, 56, 3572-3582.
    • (1991) J. Org. Chem. , Issue.56 , pp. 3572-3582
    • Ireland, R.E.1    Wipf, P.2    Xiang, J.-N.3
  • 14
    • 0001997183 scopus 로고
    • The ireland-claisen rearrangement
    • Pereira, S.; Srebnik, M. The Ireland-Claisen rearrangement. Aldrichim. Acta 1993, 26, 17-29.
    • (1993) Aldrichim. Acta , vol.26 , pp. 17-29
    • Pereira, S.1    Srebnik, M.2
  • 15
    • 37049121526 scopus 로고
    • The reformatsky-claisen reaction, a new synthetically useful sigmatropic process
    • Baldwin, J.E.; Walker, J.A. The Reformatsky-Claisen reaction, A new synthetically useful sigmatropic process. J. Chem. Soc. Chem. Commun. 1973, 117-118.
    • (1973) J. Chem. Soc. Chem. Commun. , pp. 117-118
    • Baldwin, J.E.1    Walker, J.A.2
  • 16
    • 4344562388 scopus 로고
    • A new synthesis of medium-membered lactones via intramolecular condensation of α-chlorosulfides containing an ester group and allylsilanyl moiety
    • Wada, M.; Shigehisa, T.; Akiba, K. A new synthesis of medium-membered lactones via intramolecular condensation of α-chlorosulfides containing an ester group and allylsilanyl moiety. Tetrahedron Lett. 1985, 26, 5191-5194.
    • (1985) Tetrahedron Lett. , vol.26 , pp. 5191-5194
    • Wada, M.1    Shigehisa, T.2    Akiba, K.3
  • 17
    • 0037684968 scopus 로고    scopus 로고
    • Synthesis of polycyclic imines by palladium-catalyzed domino cyclization of di- and trienyl ketone o-pentafluorobenzoyloximes
    • Zaman, S.; Kitamura, M.; Narasaka, K. Synthesis of polycyclic imines by palladium-catalyzed domino cyclization of di- and trienyl ketone O-pentafluorobenzoyloximes. Bull. Chem. Soc. Jpn. 2003, 76, 1055-1062.
    • (2003) Bull. Chem. Soc. Jpn. , vol.76 , pp. 1055-1062
    • Zaman, S.1    Kitamura, M.2    Narasaka, K.3
  • 18
    • 0001210319 scopus 로고
    • Fluorine-containing organozinc reagents. V.1: The reformatskii-claisen reaction of chlorodifluoroacetic acid derivatives
    • Greuter, H.; Lang, R.W.; Romann, A.J. Fluorine-containing organozinc reagents. V.1: The Reformatskii-claisen reaction of chlorodifluoroacetic acid derivatives. Tetrahedron Lett. 1988, 29, 3291-3294.
    • (1988) Tetrahedron Lett. , Issue.29 , pp. 3291-3294
    • Greuter, H.1    Lang, R.W.2    Romann, A.J.3
  • 20
    • 61849130681 scopus 로고    scopus 로고
    • Stereoselective reformatskii-claisen rearrangement: Synthesis of 2',3'-dideoxy-6',6'-difluoro-2'-thionucleosides
    • Zheng, F.; Zhang, X.; Qing, F.-L. Stereoselective Reformatskii-Claisen rearrangement: Synthesis of 2',3'-dideoxy-6',6'-difluoro-2'-thionucleosides. Chem. Commun. 2009, 1505-1507.
    • (2009) Chem. Commun. , pp. 1505-1507
    • Zheng, F.1    Zhang, X.2    Qing, F.-L.3
  • 21
    • 38349083548 scopus 로고    scopus 로고
    • Synthesis of 3',3'-difluoro- 2'-hydroxymethyl-4',5'-unsaturated carbocyclic nucleosides
    • Yang, Y.-Y.; Xu, J.; You, Z.-W.; Xu, X.-H.; Qiu, X.-L.; Qing, F.-L. Synthesis of 3',3'-difluoro- 2'-hydroxymethyl-4',5'-unsaturated carbocyclic nucleosides. Org. Lett. 2007, 9, 5437-5440.
    • (2007) Org. Lett. , vol.9 , pp. 5437-5440
    • Yang, Y.-Y.1    Xu, J.2    You, Z.-W.3    Xu, X.-H.4    Qiu, X.-L.5    Qing, F.-L.6
  • 22
    • 79955039548 scopus 로고    scopus 로고
    • Synthesis of 2',3'-dideoxy-6'-fluorocarbocyclic nucleosides via reformatskii-claisen rearrangement
    • Yang, Y.; Zheng, F.; Qing, F.-L. Synthesis of 2',3'-dideoxy-6'- fluorocarbocyclic nucleosides via Reformatskii-Claisen rearrangement. Tetrahedron 2011, 67, 3388-3394.
    • (2011) Tetrahedron , vol.67 , pp. 3388-3394
    • Yang, Y.1    Zheng, F.2    Qing, F.-L.3
  • 23
    • 69549096588 scopus 로고    scopus 로고
    • A new variant of reformatsky-claisen rearrangement mediated by indium chloride
    • Ishihara, J.; Koyama, N.; Nishino, Y.; Takahashi, K.; Hatakeyama, S. A new variant of Reformatsky-Claisen rearrangement mediated by indium chloride. Synlett 2009, 2351-2355.
    • (2009) Synlett , pp. 2351-2355
    • Ishihara, J.1    Koyama, N.2    Nishino, Y.3    Takahashi, K.4    Hatakeyama, S.5
  • 25
    • 33847802004 scopus 로고
    • Activated metals. Ix. New reformatsky reagent involving activated indium for the preparation of β-hydroxy esters
    • Chao, L.-C.; Rieke, R.D. Activated metals. IX. New reformatsky reagent involving activated indium for the preparation of β-hydroxy esters. J. Org. Chem. 1975, 40, 2253-2255.
    • (1975) J. Org. Chem. , vol.40 , pp. 2253-2255
    • Chao, L.-C.1    Rieke, R.D.2
  • 26
    • 10044234065 scopus 로고    scopus 로고
    • In- or in (i)-employed diastereoselective reformatsky-type reactions with ketones:1h-nmr investigations on the active species
    • Babu, S.A.; Yasuda, M.; Shibata, I.; Baba, A. In- or In(I)-Employed diastereoselective Reformatsky-type reactions with ketones:1H-NMR investigations on the active species. Org. Lett. 2004, 6, 4475-4478.
    • (2004) Org. Lett. , vol.6 , pp. 4475-4478
    • Babu, S.A.1    Yasuda, M.2    Shibata, I.3    Baba, A.4
  • 27
    • 28744445551 scopus 로고    scopus 로고
    • In- or in (i)-employed tailoring of the stereogenic centers in the reformatsky-type reactions of simple ketones, α-Alkoxy ketones, and β-keto esters
    • Babu, S.A.; Yasuda, M.; Shibata, I.; Baba, A. In- or In(I)-employed tailoring of the stereogenic centers in the Reformatsky-type reactions of simple ketones, α-Alkoxy ketones, and β-keto esters. J. Org. Chem. 2005, 70, 10408-10419.
    • (2005) J. Org. Chem. , vol.70 , pp. 10408-10419
    • Babu, S.A.1    Yasuda, M.2    Shibata, I.3    Baba, A.4
  • 28
    • 33746603961 scopus 로고    scopus 로고
    • High chelation control of three contiguous stereogenic centers in the reformatsky reactions of indium enolates with α-hydroxy ketones: Unexpected stereochemistry of lactone formation
    • Babu, S.A.; Yasuda, M.; Okabe, Y.; Shibata, I.; Baba, A. High chelation control of three contiguous stereogenic centers in the Reformatsky reactions of indium enolates with α-hydroxy ketones: Unexpected stereochemistry of lactone formation. Org. Lett. 2006, 8, 3029-3032.
    • (2006) Org. Lett. , vol.8 , pp. 3029-3032
    • Babu, S.A.1    Yasuda, M.2    Okabe, Y.3    Shibata, I.4    Baba, A.5
  • 31
    • 76349095819 scopus 로고    scopus 로고
    • Syn-effect" in the base-induced isomerization of vinylic sulfones to allylic sulfones and the related various reactions
    • Inomata, K. "Syn-effect" in the base-induced isomerization of vinylic sulfones to allylic sulfones and the related various reactions. J. Synth. Org. Chem. Jpn. 2009, 67, 1172-1182.
    • (2009) J. Synth. Org. Chem. Jpn. , vol.67 , pp. 1172-1182
    • Inomata, K.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.