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Volumn 19, Issue 5, 2008, Pages 603-606

Triorganozincates as efficient nucleophiles for the diastereoselective addition to N-(tert-butanesulfinyl)imines

Author keywords

[No Author keywords available]

Indexed keywords

GRIGNARD REAGENT; IMINE; MAGNESIUM DERIVATIVE; METHYL GROUP; N (TERT BUTANESULFINYL)BENZALDIMINE; N (TERT BUTANESULFINYL)IMINE; ORGANOMETALLIC COMPOUND; SULFINAMIDE; TRIORGANOZINCATE DERIVATIVE; UNCLASSIFIED DRUG; ZINC DERIVATIVE;

EID: 40849146803     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2008.01.038     Document Type: Article
Times cited : (41)

References (32)
  • 9
    • 33845675615 scopus 로고
    • Trost B.M., Fleming I., and Shreiber S.L. (Eds), Pergamon Press, Oxford Chapter 1.7
    • Knochel P. In: Trost B.M., Fleming I., and Shreiber S.L. (Eds). Comprehensive Organic Synthesis Vol. 1 (1991), Pergamon Press, Oxford Chapter 1.7
    • (1991) Comprehensive Organic Synthesis , vol.1
    • Knochel, P.1
  • 12
    • 33748247006 scopus 로고
    • 2Zn and RZnX reagents react sluggishly with aldehydes and not at all with ketones. See, for instance:
    • 2Zn and RZnX reagents react sluggishly with aldehydes and not at all with ketones. See, for instance:. Noyori R., and Kitamura M. Angew. Chem., Int. Ed. Engl. 30 (1991) 49-69
    • (1991) Angew. Chem., Int. Ed. Engl. , vol.30 , pp. 49-69
    • Noyori, R.1    Kitamura, M.2
  • 13
    • 0003417469 scopus 로고
    • Trost B.M., Fleming I., and Semmelhack M.F. (Eds), Pergamon Press, Oxford Section 1.2.2.1.4
    • Lee V.J. In: Trost B.M., Fleming I., and Semmelhack M.F. (Eds). Comprehensive Organic Synthesis Vol. 4 (1991), Pergamon Press, Oxford Section 1.2.2.1.4
    • (1991) Comprehensive Organic Synthesis , vol.4
    • Lee, V.J.1
  • 24
    • 40849084293 scopus 로고    scopus 로고
    • See also Ref. 5c.
    • See also Ref. 5c.
  • 25
    • 40849112177 scopus 로고    scopus 로고
    • note
    • The low transfer ability of the methyl group from triorganozincates has been shown in other addition reactions. For instance, see Refs. 3c and 4b.
  • 26
    • 0037189199 scopus 로고    scopus 로고
    • 3ZnLi and di-tert-butyl ketone, see:
    • 3ZnLi and di-tert-butyl ketone, see:. Maclin K.M., and Richey Jr. H.G. J. Org. Chem. 67 (2002) 4602-4604
    • (2002) J. Org. Chem. , vol.67 , pp. 4602-4604
    • Maclin, K.M.1    Richey Jr., H.G.2
  • 27
    • 40849134668 scopus 로고    scopus 로고
    • note
    • A referee suggested that the determination of the relative proportion of 2 and 3 by HPLC using UV detection is an estimate unless it has been proven that both diastereoisomers have the same UV response. The fact that the enantiomeric ratios of the free primary amines are equal to the corresponding 2:3 diastereomeric ratios determined by HPLC indicates that the latter technique is appropriate for determining the diastereomeric ratio of this kind of sulfinamides.
  • 28
    • 40849115358 scopus 로고    scopus 로고
    • note
    • The retention times for the other addition products under the same elution conditions were 7.9 (2b), 9.7 (3b), 7.8 (2c), 12.1 (3c), 9.5 (2d) and 11.1 (3d).
  • 30
    • 0032546885 scopus 로고    scopus 로고
    • 20 = + 4.3 [(c 1.6) EtOH, 90.2% ee (R)]. Ref.:
    • 20 = + 4.3 [(c 1.6) EtOH, 90.2% ee (R)]. Ref.:. Bataille P., Paterne M., and Brown E. Tetrahedron: Asymmetry 9 (1998) 2181-2192
    • (1998) Tetrahedron: Asymmetry , vol.9 , pp. 2181-2192
    • Bataille, P.1    Paterne, M.2    Brown, E.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.