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Volumn 65, Issue 6, 2000, Pages 1702-1706

Asymmetric samarium-reformatsky reaction of chiral α-bromoacetyl-2- oxazolidinones with aldehydes

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; BENZALDEHYDE; CARBOXYLIC ACID; LITHIUM DERIVATIVE; OXAZOLIDINONE DERIVATIVE; REAGENT; SAMARIUM; TITANIUM DERIVATIVE;

EID: 0034708574     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9914317     Document Type: Article
Times cited : (105)

References (48)
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    • For examples for metal and metal salts reagents, see the following. (a) Al: Maruoka, K.; Hashimoto, S.; Kitagawa, Y.; Yamamoto, H. J. Am. Chem. Soc. 1977, 99, 7705; Bull. Chem. Soc. Jpn. 1980, 53, 3301. Matsubara, S.; Tsuboniwa, N.; Morizawa, Y.; Oshima, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1984, 57, 3242.
    • (1980) Bull. Chem. Soc. Jpn. , vol.53 , pp. 3301
  • 5
    • 0021521001 scopus 로고
    • For examples for metal and metal salts reagents, see the following. (a) Al: Maruoka, K.; Hashimoto, S.; Kitagawa, Y.; Yamamoto, H. J. Am. Chem. Soc. 1977, 99, 7705; Bull. Chem. Soc. Jpn. 1980, 53, 3301. Matsubara, S.; Tsuboniwa, N.; Morizawa, Y.; Oshima, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1984, 57, 3242.
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    • (b) Ce: Imamoto, T.; Kusumoto, T.; Tawarayama, Y.; Sugiura, Y.; Mita, T.; Hatanaka, Y.; Yokoyama, M. J. Org. Chem. 1984, 49, 3904. Fukuzawa, S.; Tsuruta, T.; Fujinami, T.; Sakai, S. J. Chem. Soc., Perkin Trans. 1 1987, 1473; Fukuzawa, S.; Hirai, K. J. Chem. Soc., Perkin Trans. 1 1993, 1963.
    • (1987) J. Chem. Soc., Perkin Trans. 1 , pp. 1473
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  • 8
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    • (b) Ce: Imamoto, T.; Kusumoto, T.; Tawarayama, Y.; Sugiura, Y.; Mita, T.; Hatanaka, Y.; Yokoyama, M. J. Org. Chem. 1984, 49, 3904. Fukuzawa, S.; Tsuruta, T.; Fujinami, T.; Sakai, S. J. Chem. Soc., Perkin Trans. 1 1987, 1473; Fukuzawa, S.; Hirai, K. J. Chem. Soc., Perkin Trans. 1 1993, 1963.
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    • Molander, G.A.1    Harris, C.H.2
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    • Chiral 1,1,2-triphenylethanediol has been reported as a useful chiral auxiliary for aldol reaction. Braun, M.; Graf, S.; Herzog, S. Org. Synth. 1995, 72, 32; 42.
    • (1995) Org. Synth. , vol.72 , pp. 32
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  • 31
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    • Ager, D.J.1    Prakash, I.2    Schaad, D.R.3
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    • For a review on chiral oxazolidinones in asymmetric synthesis: Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835- 875; Aldrichim. Acta 1997, 30(1), 3.
    • (1997) Aldrichim. Acta , vol.30 , Issue.1 , pp. 3
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    • note
    • 13
  • 48
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    • note
    • Addition of more than 4 equiv of hexamethylphosphoric amide to samarium(II) iodide remarkably decreased the diastereoselectivity (59% de) in 7a, suggesting the chelation control should be involved in the high diastereoselectivity.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.