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Volumn 3, Issue 8-9, 2008, Pages 1500-1504

Catalytic asymmetric epoxidation of α,β-unsaturated phosphane oxides with a Y(O-iPr)3/biphenyldiol complex

Author keywords

Asymmetric catalysis; Biaryldiols; Epoxidation; Organo phosphorus compounds; Yttrium

Indexed keywords

EPOXIDE; OXIDE; PHENOL DERIVATIVE; PHOSPHINE; PHOSPHINE DERIVATIVE; YTTRIUM;

EID: 54849411260     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.200800035     Document Type: Article
Times cited : (39)

References (55)
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    • Catalytic asymmetric dihydroxylation of α,β-unsaturated phosphonates as a key step: Y. Kobayashi, A. D. William, Y. Tokoro, J. Org. Chem. 2001, 66, 7903, and references therein.
    • Catalytic asymmetric dihydroxylation of α,β-unsaturated phosphonates as a key step: Y. Kobayashi, A. D. William, Y. Tokoro, J. Org. Chem. 2001, 66, 7903, and references therein.
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    • Recent general reviews on asymmetric epoxidations: a) Modern Oxidation Methods (Ed.: J. E. Bäckvall), Wiley-VCH, Weinheim, 2004;
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    • For recent general reviews on asymmetric epoxidation of electrondeficient C-C double bonds, see: a
    • For recent general reviews on asymmetric epoxidation of electrondeficient C-C double bonds, see: a) M. J. Porter, J. Skidmore, Chem. Commun. 2000, 1215;
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    • The synthesis of functionalized chiral phosphane oxides is also useful owing to their potential use in asymmetric catalysis; see the review: a M. Kanai, N. Kato, E. Ichikawa, M. Shibasaki, Synlett 2005, 1491;
    • The synthesis of functionalized chiral phosphane oxides is also useful owing to their potential use in asymmetric catalysis; see the review: a) M. Kanai, N. Kato, E. Ichikawa, M. Shibasaki, Synlett 2005, 1491;
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    • for selected recent examples, see also: b) I. Fujimori, T. Mita, K. Maki, M. Shiro, A. Sato, S. Furusho, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2006, 128, 16438;
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    • 3P(O) additive had beneficial effects on epoxidation, see: a) T. Kinoshita, S. Okada, S.-R. Park, S. Matsunaga, M. Shibasaki, Angew. Chem. 2003, 115, 4828;
    • 3P(O) additive had beneficial effects on epoxidation, see: a) T. Kinoshita, S. Okada, S.-R. Park, S. Matsunaga, M. Shibasaki, Angew. Chem. 2003, 115, 4828;
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    • for a general review of achiral additives for the improvement of chiral catalysts, see: b
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    • Steric and electronic modification of phosphane oxide additives have beneficial effects in rare-earth-metal-catalyzed epoxidation as well as other reactions; see, for epoxidation: a R. Kino, K. Daikai, T. Kawanami, H. Furuno, J. Inanaga, Org. Biomol. Chem. 2004, 2, 1822;
    • Steric and electronic modification of phosphane oxide additives have beneficial effects in rare-earth-metal-catalyzed epoxidation as well as other reactions; see, for epoxidation: a) R. Kino, K. Daikai, T. Kawanami, H. Furuno, J. Inanaga, Org. Biomol. Chem. 2004, 2, 1822;
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    • Biphenyldiol 1a: a A. I. Meyers, T. D. Nelson, H. Moorlag, D. J. Rawson, A. Meier, Tetrahedron 2004, 60, 4459, and references therein;
    • Biphenyldiol 1a: a) A. I. Meyers, T. D. Nelson, H. Moorlag, D. J. Rawson, A. Meier, Tetrahedron 2004, 60, 4459, and references therein;
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    • We selected Ph(2-MeO-C6H4)2P(O) as the best additive for further studies. When β-alkyl α,β-unsaturated phosphane oxide 2 f was used as a substrate, Ph(2-MeO-C6H 4)2P(O) also gave slightly better results than Ph 3P(O, Ph(2-MeO-C6H4)2P(O, 98% yield, 91% ee (see Table 2, Ph3PO, 80% yield, 87% ee
    • 3P(O): 80% yield, 87% ee.
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    • 3As(O) has adverse effects on the reactivity of the rare-earth-metal catalyst; see references [10b] and [16].
    • 3As(O) has adverse effects on the reactivity of the rare-earth-metal catalyst; see references [10b] and [16].
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    • The absolute configurations of epoxides 3a and 3 f were determined to be S,S after epoxide ring opening; see Supporting Information for detailed information.
    • The absolute configurations of epoxides 3a and 3 f were determined to be S,S after epoxide ring opening; see Supporting Information for detailed information.
  • 55
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    • 3 of the same quality is also available from Aldrich (Cat. No. 2172-12-5); see also: M. Shibasaki, M. Kanai, S. Matsunaga, Aldrichimica Acta 2006, 39, 31.
    • 3 of the same quality is also available from Aldrich (Cat. No. 2172-12-5); see also: M. Shibasaki, M. Kanai, S. Matsunaga, Aldrichimica Acta 2006, 39, 31.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.