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Volumn 68, Issue 8, 2003, Pages 3360-3362

Single route to chiral syn- and anti-2-amino-1,2-diphenylethanols via a new stereodivergent opening of trans-1,2-diphenyloxirane

Author keywords

[No Author keywords available]

Indexed keywords

MAGNESIUM COMPOUNDS; OXIDES; POTASSIUM COMPOUNDS; SODIUM COMPOUNDS;

EID: 0037453562     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034133p     Document Type: Article
Times cited : (30)

References (31)
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    • For more recent reviews, see: (a) Ager, D. J.; Prakash, I.; Schaad, R. R. Chem. Rev. 1996, 96, 835. (b) Bergmeier, S. C. Tetrahedron 2000, 56, 2561. (c) Bonini, C.; Righi, G. Tetrahedron 2002, 58, 4981.
    • (2000) Tetrahedron , vol.56 , pp. 2561
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    • For more recent reviews, see: (a) Ager, D. J.; Prakash, I.; Schaad, R. R. Chem. Rev. 1996, 96, 835. (b) Bergmeier, S. C. Tetrahedron 2000, 56, 2561. (c) Bonini, C.; Righi, G. Tetrahedron 2002, 58, 4981.
    • (2002) Tetrahedron , vol.58 , pp. 4981
    • Bonini, C.1    Righi, G.2
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    • note
    • Price ranges between 40 and 100 Euros/g in the Aldrich catalogue, depending on the isomer.
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    • For the preparation of the (R,R)-epoxide see: (a) Tu, Y.; Wang, Z.-X.; Shi, Y. J. Am. Chem. Chem. 1996, 118, 9806 (73% yield, >95% ee, from trans-stilbene). (b) Solladié-Cavallo, A.; Roje, M.; Isarno, T.; Sunjic, V.; Vinkovic, V. Eur. J. Org. Chem. 2000, 1077 (70% yield, 97% ee, from benzaldeyde). For the preparation of the (S,S)-epoxide from trans-stilbene, see: Solladié-Cavallo, A.; Bouerat, L.; Jierry, L. Eur. J. Org. Chem. 2001, 4557 (90% yield, 90% ee).
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  • 19
    • 0042290869 scopus 로고    scopus 로고
    • For the preparation of the (R,R)-epoxide see: (a) Tu, Y.; Wang, Z.-X.; Shi, Y. J. Am. Chem. Chem. 1996, 118, 9806 (73% yield, >95% ee, from trans-stilbene). (b) Solladié-Cavallo, A.; Roje, M.; Isarno, T.; Sunjic, V.; Vinkovic, V. Eur. J. Org. Chem. 2000, 1077 (70% yield, 97% ee, from benzaldeyde). For the preparation of the (S,S)-epoxide from trans-stilbene, see: Solladié-Cavallo, A.; Bouerat, L.; Jierry, L. Eur. J. Org. Chem. 2001, 4557 (90% yield, 90% ee).
    • (2000) Eur. J. Org. Chem. , pp. 1077
    • Solladié-Cavallo, A.1    Roje, M.2    Isarno, T.3    Sunjic, V.4    Vinkovic, V.5
  • 20
    • 0035215391 scopus 로고    scopus 로고
    • For the preparation of the (R,R)-epoxide see: (a) Tu, Y.; Wang, Z.-X.; Shi, Y. J. Am. Chem. Chem. 1996, 118, 9806 (73% yield, >95% ee, from trans-stilbene). (b) Solladié-Cavallo, A.; Roje, M.; Isarno, T.; Sunjic, V.; Vinkovic, V. Eur. J. Org. Chem. 2000, 1077 (70% yield, 97% ee, from benzaldeyde). For the preparation of the (S,S)-epoxide from trans-stilbene, see: Solladié-Cavallo, A.; Bouerat, L.; Jierry, L. Eur. J. Org. Chem. 2001, 4557 (90% yield, 90% ee).
    • (2001) Eur. J. Org. Chem. , pp. 4557
    • Solladié-Cavallo, A.1    Bouerat, L.2    Jierry, L.3
  • 21
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    • For reviews on metal halide opening of oxiranes and aziridines, see: (a) Bonini, C.; Righi, G. Synthesis 1994, 225. (b) Righi, G.; Bonini, C. In Targets in Heterocyclic Systems, Chemistry and Properties; Attanasi, O. A.; Spinelli, D., Eds.; Italian Society of Chemistry: Roma, 2001; Vol. 4, p 139.
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    • Attanasi, O. A.; Spinelli, D., Eds.; Italian Society of Chemistry: Roma
    • For reviews on metal halide opening of oxiranes and aziridines, see: (a) Bonini, C.; Righi, G. Synthesis 1994, 225. (b) Righi, G.; Bonini, C. In Targets in Heterocyclic Systems, Chemistry and Properties; Attanasi, O. A.; Spinelli, D., Eds.; Italian Society of Chemistry: Roma, 2001; Vol. 4, p 139.
    • (2001) Targets in Heterocyclic Systems, Chemistry and Properties , vol.4 , pp. 139
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    • note
    • 1H NMR analysis of the mixture of the epoxides obtained.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.