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Volumn 38, Issue 23, 1999, Pages 3504-3506

The first catalytic asymmetric nitro-Mannich-type reaction promoted by a new heterobimetallic complex

Author keywords

Asymmetric catalysis; Asymmetric synthesis; Diamines; Imines; Nitroalkanes

Indexed keywords

DIAMINE; IMINE; METAL COMPLEX; NITROALKANE;

EID: 0033521210     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19991203)38:23<3504::AID-ANIE3504>3.0.CO;2-E     Document Type: Article
Times cited : (234)

References (38)
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    • For leading references in this field since 1996, see a) T. Suzuki, T. Shibata, K. Soai, J. Chem. Soc. Perkin Trans. 1 1997, 2757; b) T. Hayase, S. Osanai, T. Shibata, K. Soai, Heterocycles 1998, 48, 139; P. G. Anderson, D. Guijarro, D. Tanner, J. Org. Chem. 1997, 62, 7364.
    • (1997) J. Chem. Soc. Perkin Trans. 1 , pp. 2757
    • Suzuki, T.1    Shibata, T.2    Soai, K.3
  • 6
    • 0000479895 scopus 로고    scopus 로고
    • For leading references in this field since 1996, see a) T. Suzuki, T. Shibata, K. Soai, J. Chem. Soc. Perkin Trans. 1 1997, 2757; b) T. Hayase, S. Osanai, T. Shibata, K. Soai, Heterocycles 1998, 48, 139; P. G. Anderson, D. Guijarro, D. Tanner, J. Org. Chem. 1997, 62, 7364.
    • (1998) Heterocycles , vol.48 , pp. 139
    • Hayase, T.1    Osanai, S.2    Shibata, T.3    Soai, K.4
  • 7
    • 0001010190 scopus 로고    scopus 로고
    • For leading references in this field since 1996, see a) T. Suzuki, T. Shibata, K. Soai, J. Chem. Soc. Perkin Trans. 1 1997, 2757; b) T. Hayase, S. Osanai, T. Shibata, K. Soai, Heterocycles 1998, 48, 139; P. G. Anderson, D. Guijarro, D. Tanner, J. Org. Chem. 1997, 62, 7364.
    • (1997) J. Org. Chem. , vol.62 , pp. 7364
    • Anderson, P.G.1    Guijarro, D.2    Tanner, D.3
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    • b) H. Ishitani, S. Komiyama, S. Kobayashi, Angew. Chem. 1998, 110, 3369; Angew. Chem. Int. Ed. 1998, 37, 3186;
    • (1998) Angew. Chem. Int. Ed. , vol.37 , pp. 3186
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    • 0030788440 scopus 로고    scopus 로고
    • Review: M. Shibasaki, H. Sasai, T. Arai, Angew. Chem. 1997, 109, 1290; Angew. Chem. Int. Ed. Engl. 1997, 36, 1236.
    • (1997) Angew. Chem. Int. Ed. Engl. , vol.36 , pp. 1236
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    • note
    • 3] (LLB) as catalyst.
  • 26
    • 0344766323 scopus 로고    scopus 로고
    • note
    • 2, (1.0M, 0.55 mL) was added dropwise to the cooled mixture (over ca. 5 min). After the removal of the ice-water bath, the mixture was stirred for 2 h at room temperature, and then diluted with toluene (ca. 20 mL). The mixture was transferred into a 200-mL flask, and was diluted with further toluene (ca. 75 mL). The suspension was then filtered through celite, and the celite was washed with toluene. Evaporation of the solvent gave a brown oil containing mainly the imine 1a and benzaldehyde. The excess benzaldehyde was removed under high vacuum, and recrystallization of the resulting solid provided the imine 1a (0.26 g, 85%).
  • 27
    • 0344766321 scopus 로고    scopus 로고
    • note
    • 2] (ALB) gave no product.
  • 28
    • 0344766322 scopus 로고    scopus 로고
    • When nitromethane was added in one portion, the result was less satisfactory (34% yield, 45% ee)
    • When nitromethane was added in one portion, the result was less satisfactory (34% yield, 45% ee).
  • 29
    • 0344766320 scopus 로고    scopus 로고
    • This is a characteristic structure for heterobimetallic complexes with a Group 13 central metal
    • This is a characteristic structure for heterobimetallic complexes with a Group 13 central metal.
  • 30
    • 0345196810 scopus 로고    scopus 로고
    • note
    • To overcome these problems of reactivity, bis(4-trifluoromethylphenyl)phosphinoyl imines were prepared. However, this strategy was unsuccessful, and did not give better results.
  • 31
    • 0344766319 scopus 로고    scopus 로고
    • note
    • Attempts to prepare the corresponding imines starting from enolizable aldehydes, such as isobutyraldehyde, failed due to self-condensation of the aldehydes under the conditions of imine formation.
  • 37
    • 0345628818 scopus 로고    scopus 로고
    • Address: 5-1-28, Chiyoda, Sakato, Saitama 350-02 (Japan); Fax: (+ 81)492-84-1351
    • Address: 5-1-28, Chiyoda, Sakato, Saitama 350-02 (Japan); Fax: (+ 81)492-84-1351.
  • 38
    • 0344766317 scopus 로고    scopus 로고
    • note
    • 1, retention time: 15 min (S isomer) and 27 min (R isomer), detection at 254 nm).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.