메뉴 건너뛰기




Volumn 23, Issue 2, 2011, Pages 167-171

Geometric enantiomerism in cyclic compounds: Chiral dibrominated 1,3-dioxanes

Author keywords

1,3 dioxanes; chiral HPLC; diastereoselective bromination; geometric enantiomers; X ray structures

Indexed keywords

1,3 DIOXANE DERIVATIVE;

EID: 78650932871     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.20895     Document Type: Article
Times cited : (4)

References (32)
  • 6
    • 0020169638 scopus 로고
    • Basic principles of the CIP-system and proposals for a revision
    • Prelog V, Helmchen G,. Basic principles of the CIP-system and proposals for a revision. Angew Chem Int Ed Engl 1982; 21: 567-583.
    • (1982) Angew Chem Int Ed Engl , vol.21 , pp. 567-583
    • Prelog, V.1    Helmchen, G.2
  • 8
    • 0038462466 scopus 로고
    • Resolution of 2,6-diphenyl-1-methyl-4-piperidone oxime, a novel example of molecular isomerism
    • Lyle RE, Lyle GG,. Resolution of 2,6-diphenyl-1-methyl-4-piperidone oxime, a novel example of molecular isomerism. J Org Chem 1959; 24: 1679-1684.
    • (1959) J Org Chem , vol.24 , pp. 1679-1684
    • Lyle, R.E.1    Lyle, G.G.2
  • 9
    • 0008585811 scopus 로고
    • The absolute configuration of (+)-1-methyl-2,6-diphenyl-4-piperidone oxime
    • Lyle GG, Pelosi ET,. The absolute configuration of (+)-1-methyl-2,6- diphenyl-4-piperidone oxime. J Am Chem Soc 1966; 88: 5276-5279.
    • (1966) J Am Chem Soc , vol.88 , pp. 5276-5279
    • Lyle, G.G.1    Pelosi, E.T.2
  • 10
    • 49949139810 scopus 로고
    • Resolution of (±)-tropinone oxime
    • Singh H, Razdan B,. Resolution of (±)-tropinone oxime. Tetrahedron Lett 1966; 28: 3243-3245.
    • (1966) Tetrahedron Lett , vol.28 , pp. 3243-3245
    • Singh, H.1    Razdan, B.2
  • 11
    • 30944468309 scopus 로고    scopus 로고
    • Cis-trans Enantiomerism in the Diels-Alder cycloadducts of 6-arylfulvenes with maleic anhydride: Resolution of the exo adducts via the N-((1S)-1-(naphth-1-yl)ethyl)imide derivatives: Assignment of the absolute configurations based on the crystal structure of an imide diastereomer
    • Chandrasekhar S, Gorla SK,. cis-trans Enantiomerism in the Diels-Alder cycloadducts of 6-arylfulvenes with maleic anhydride: resolution of the exo adducts via the N-((1S)-1-(naphth-1-yl)ethyl)imide derivatives: assignment of the absolute configurations based on the crystal structure of an imide diastereomer. Tetrahedron: Asymmetry 2006; 17: 92-98.
    • (2006) Tetrahedron: Asymmetry , vol.17 , pp. 92-98
    • Chandrasekhar, S.1    Gorla, S.K.2
  • 12
    • 0033082647 scopus 로고    scopus 로고
    • Enantioselective inclusion complexation of N-nitrosopiperidines by steroidal bile acids
    • Gdaniec M, Milewska MJ, Połonski T,. Enantioselective inclusion complexation of N-nitrosopiperidines by steroidal bile acids. Angew Chem Int Ed Engl 1999; 38: 392-395.
    • (1999) Angew Chem Int Ed Engl , vol.38 , pp. 392-395
    • Gdaniec, M.1    Milewska, M.J.2    Połonski, T.3
  • 13
    • 27944485776 scopus 로고    scopus 로고
    • Thioamides and selenoamides with chirality solely due to hindered rotation about the C-N bond: Enantioselective complexation with optically active hosts
    • Olszewska T, Pyszno A, Milewska MJ, Gdaniec M, Połonski T,. Thioamides and selenoamides with chirality solely due to hindered rotation about the C-N bond: enantioselective complexation with optically active hosts. Tetrahedron: Asymmetry 2005; 16: 3711-3717.
    • (2005) Tetrahedron: Asymmetry , vol.16 , pp. 3711-3717
    • Olszewska, T.1    Pyszno, A.2    Milewska, M.J.3    Gdaniec, M.4    Połonski, T.5
  • 14
    • 37649026114 scopus 로고    scopus 로고
    • TADDOLs, their derivatives, and TADDOL analogues: Versatile chiral auxiliaries
    • Seebach D, Beck AK, Heckel A,. TADDOLs, their derivatives, and TADDOL analogues: versatile chiral auxiliaries. Angew Chem Int Ed Engl 2001; 40: 92-138.
    • (2001) Angew Chem Int Ed Engl , vol.40 , pp. 92-138
    • Seebach, D.1    Beck, A.K.2    Heckel, A.3
  • 15
    • 0034701323 scopus 로고    scopus 로고
    • Switching a helical polymer between mirror images using circularly polarized light
    • Li J, Schuster GB, Cheon K-S, Green MM, Selinger JV,. Switching a helical polymer between mirror images using circularly polarized light. J Am Chem Soc 2000; 122: 2603-2612.
    • (2000) J Am Chem Soc , vol.122 , pp. 2603-2612
    • Li, J.1    Schuster, G.B.2    Cheon, K.-S.3    Green, M.M.4    Selinger, J.V.5
  • 16
    • 4544323687 scopus 로고    scopus 로고
    • Asymmetric synthesis utilizing circulary polarized light mediated by the photoequilibrium of chiral olefins in conjunction with asymmetric autocatalysis
    • Sato I, Sugie R, Matsueda Y, Furumura Y, Saoai K,. Asymmetric synthesis utilizing circulary polarized light mediated by the photoequilibrium of chiral olefins in conjunction with asymmetric autocatalysis. Angew Chem Int Ed Engl 2004; 43: 4490-4492.
    • (2004) Angew Chem Int Ed Engl , vol.43 , pp. 4490-4492
    • Sato, I.1    Sugie, R.2    Matsueda, Y.3    Furumura, Y.4    Saoai, K.5
  • 17
    • 0028953343 scopus 로고
    • Synthesis and stereochemistry of some new chiral brominated 1,3-dioxanes
    • Grosu I, Plé G, Mager S,. Synthesis and stereochemistry of some new chiral brominated 1,3-dioxanes. Tetrahedron 1995; 51: 2659-2672.
    • (1995) Tetrahedron , vol.51 , pp. 2659-2672
    • Grosu, I.1    Plé, G.2    Mager, S.3
  • 18
    • 0034391149 scopus 로고    scopus 로고
    • Synthesis and stereochemistry of novel dibrominated 1,5-dioxaspiro[5.5] undecane derivatives
    • Grosu I, Toupet L, Plé G, Mager S, Mesaros E, Varga A, Bogdan E,. Synthesis and stereochemistry of novel dibrominated 1,5-dioxaspiro[5.5]undecane derivatives. Monatsh Chem 2000; 131: 277-286.
    • (2000) Monatsh Chem , vol.131 , pp. 277-286
    • Grosu, I.1    Toupet, L.2    Plé, G.3    Mager, S.4    Mesaros, E.5    Varga, A.6    Bogdan, E.7
  • 20
  • 21
  • 22
    • 0032823740 scopus 로고    scopus 로고
    • Synthesis of 1-bromo-3-buten-2-one
    • Westerlund A, Carlson R,. Synthesis of 1-bromo-3-buten-2-one. Synth Commun 1999; 29: 4025-4042.
    • (1999) Synth Commun , vol.29 , pp. 4025-4042
    • Westerlund, A.1    Carlson, R.2
  • 23
    • 0022625126 scopus 로고
    • Asymmetric bromination of enantiomerically pure acetals of alkyl aryl ketones
    • Castaldi G, Caviccioli S, Giordano C, Uggeri F,. Asymmetric bromination of enantiomerically pure acetals of alkyl aryl ketones. Angew Chem Int Ed Engl 1986; 25: 259-260.
    • (1986) Angew Chem Int Ed Engl , vol.25 , pp. 259-260
    • Castaldi, G.1    Caviccioli, S.2    Giordano, C.3    Uggeri, F.4
  • 24
    • 0001159705 scopus 로고
    • Tartaric acid, an efficient chiral auxiliary: New asymmetric synthesis of 2-alkyl-2-arylacetic acids
    • Castaldi G, Cavicchioli S, Giordano C, Uggeri F,. Tartaric acid, an efficient chiral auxiliary: new asymmetric synthesis of 2-alkyl-2-arylacetic acids. J Org Chem 1987; 52: 3018-3027.
    • (1987) J Org Chem , vol.52 , pp. 3018-3027
    • Castaldi, G.1    Cavicchioli, S.2    Giordano, C.3    Uggeri, F.4
  • 25
    • 0001122137 scopus 로고
    • Enantiomerically pure ketals: Diastereofacial selectivity in the halogenation of enol ethers
    • Giordano C, Coppi L, Restelli A,. Enantiomerically pure ketals: diastereofacial selectivity in the halogenation of enol ethers. J Org Chem 1990; 55: 5400-5402.
    • (1990) J Org Chem , vol.55 , pp. 5400-5402
    • Giordano, C.1    Coppi, L.2    Restelli, A.3
  • 26
    • 0034619652 scopus 로고    scopus 로고
    • Considerations on the stereoselective synthesis of dibrominated spiro-1,3-dioxanes. Synthesis and stereochemistry of monobrominated precursors
    • Bogdan E, Grosu I, Mesaros E, Toupet L, Plé G, Mager S, Muntean L,. Considerations on the stereoselective synthesis of dibrominated spiro-1,3-dioxanes. Synthesis and stereochemistry of monobrominated precursors. J Chem Soc Perkin Trans 1 2000; 3635-3639.
    • (2000) J Chem Soc Perkin Trans , vol.1 , pp. 3635-3639
    • Bogdan, E.1    Grosu, I.2    Mesaros, E.3    Toupet, L.4    Plé, G.5    Mager, S.6    Muntean, L.7
  • 27
    • 0012017886 scopus 로고
    • 2: Opposite diastereoselectivity in the bromination of enantiomerically pure ketals
    • 2: opposite diastereoselectivity in the bromination of enantiomerically pure ketals. J Org Chem 1992; 57: 2765-2766.
    • (1992) J Org Chem , vol.57 , pp. 2765-2766
    • Giordano, C.1    Coppi, L.2
  • 28
    • 0024379546 scopus 로고
    • A stereoconvergent strategy for the synthesis of enantiomerically pure (R)-(-) and (S)-(+)-2-(6-methoxy-2-naphthyl)-propanoic acid (naproxen)
    • DOI 10.1016/S0040-4020(01)81319-3
    • Giordano C, Castaldi G, Cavicchioli S, Villa M,. A stereoconvergent strategy for the synthesis of enantiomerically pure (R)-(-) and (S)-(+)-2-(6-methoxy-2-naphthyl)-propanoic acid (naproxen). Tetrahedron 1989; 45: 4243-4252. (Pubitemid 19186409)
    • (1989) Tetrahedron , vol.45 , Issue.13 , pp. 4243-4252
    • Giordano, C.1    Castaldi, G.2    Cavicchioli, S.3    Villa, M.4
  • 29
    • 0542382673 scopus 로고
    • Enantiomerically pure 2-bromoalkyl aryl ketones
    • Castaldi G, Giordano C,. Enantiomerically pure 2-bromoalkyl aryl ketones. Synthesis 1987; 1039-1042.
    • (1987) Synthesis , pp. 1039-1042
    • Castaldi, G.1    Giordano, C.2
  • 31
    • 78650954172 scopus 로고    scopus 로고
    • Synthesis and NMR spectra of some new 5-methyl-2,2-substituted-1,3- dioxanes. Studia Univ. "babes-Bolyai"
    • Muntean L, Gyorgy T, Socaci C, Grosu I, Mager S, Mihis A,. Synthesis and NMR spectra of some new 5-methyl-2,2-substituted-1,3-dioxanes. Studia Univ. "Babes-Bolyai". Chemia 2000; XL: 55-60.
    • (2000) Chemia , vol.40 , pp. 55-60
    • Muntean, L.1    Gyorgy, T.2    Socaci, C.3    Grosu, I.4    Mager, S.5    Mihis, A.6
  • 32
    • 0001256283 scopus 로고
    • A review on the conformational aspects in the 1,3-dioxane system
    • Anteunis MJO, Tavernier D, Borremans F,. A review on the conformational aspects in the 1,3-dioxane system. Heterocycles 1976; 4: 293-371.
    • (1976) Heterocycles , vol.4 , pp. 293-371
    • Anteunis, M.J.O.1    Tavernier, D.2    Borremans, F.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.