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Volumn 42, Issue 2, 1996, Pages 537-542

Dirhodium(II)tetrakis[3(S)-phthalimido-2-piperidinonate]: A novel dirhodium(II) carboxamidate catalyst for asymmetric cyclopropanation

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EID: 0000548359     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-95-s94     Document Type: Article
Times cited : (19)

References (43)
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    • (1993) Catalytic Asymmetric Synthesis
    • Ojima, I.1
  • 2
    • 0003400107 scopus 로고
    • John Wiley & Sons, New York
    • For recent books, see: (a) 'Catalytic Asymmetric Synthesis,' ed. by I. Ojima, VCH, New York, 1993. (b) R. Noyori, 'Asymmetric Catalysis in Organic Synthesis,' John Wiley & Sons, New York, 1994.
    • (1994) Asymmetric Catalysis in Organic Synthesis
    • Noyori, R.1
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    • For recent reviews, see: (a) T. Ye and M. A. McKervey, Chem. Rev., 1994, 94, 1091. (b) A. Padwa and D. J. Austin, Angew. Chem., Int. Ed. Engl., 1994, 33, 1797.
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    • Ye, T.1    McKervey, M.A.2
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    • For recent reviews, see: (a) C. Bolm, Angew. Chem., Int. Ed. Engl., 1991, 30, 542. (b) A. Togni and L. M. Venanzi, Angew. Chem., Int. Ed. Engl., 1994, 33, 497.
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    • Bolm, C.1
  • 31
    • 84988080192 scopus 로고
    • Chiral Rh(II) carboxylates-catalyzed cyclopropanations of styrene with diazoacetates have been to date unsuccessful, see: (a) H. Brunner, H. Kluschanzoff, and K. Wutz, Bull. Soc. Chim. Belg., 1989, 98, 63. (b) H. M. L. Davies and D. K. Hutcheson, Tetrahedron Lett., 1993, 34, 7243.
    • (1989) Bull. Soc. Chim. Belg. , vol.98 , pp. 63
    • Brunner, H.1    Kluschanzoff, H.2    Wutz, K.3
  • 32
    • 0027488634 scopus 로고
    • Chiral Rh(II) carboxylates-catalyzed cyclopropanations of styrene with diazoacetates have been to date unsuccessful, see: (a) H. Brunner, H. Kluschanzoff, and K. Wutz, Bull. Soc. Chim. Belg., 1989, 98, 63. (b) H. M. L. Davies and D. K. Hutcheson, Tetrahedron Lett., 1993, 34, 7243.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 7243
    • Davies, H.M.L.1    Hutcheson, D.K.2
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    • note
    • 3)].
  • 40
    • 2742528810 scopus 로고    scopus 로고
    • note
    • 13C nmr spectra, with two signals (δ 4.69 and 5.76) for the proton at the stereogenic center and two sets of signals for each carbon, suggest the (2,2-cis) geometry.
  • 41
    • 33845281753 scopus 로고
    • For a review discussing proposed mechanisms of cyclopropanations via metal-carbenes, see: M. Brookhart and W. B. Studabaker, Chem Rev., 1987, 87, 411.
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    • The sense and extent of the double diastereoselection was determined based on 7 by hplc analysis and comparison of the sign of optical rotation with the known alcohol. F. J. Impastato and H. M. Walborsky, J. Am. Chem. Soc., 1962, 84, 4838.
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    • Impastato, F.J.1    Walborsky, H.M.2
  • 43
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    • The diastereomeric excesses were determined by hplc analysis of the corresponding alcohols (10) and (11). The preferred absolute configurations of the cis-isomer (9) were determined by converting to the known dicarboxylic acid. T. Polonski, M. J. Milewska, and A. Katrusiak, J. Org. Chem., 1993, 58, 3411.
    • (1993) J. Org. Chem. , vol.58 , pp. 3411
    • Polonski, T.1    Milewska, M.J.2    Katrusiak, A.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.