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Volumn 62, Issue 51, 2006, Pages 11948-11954

Preparation of non-racemic single-stereocentre α-aminonitriles and a study of their fate in Bruylants reactions

Author keywords

[No Author keywords available]

Indexed keywords

ACID ANHYDRIDE; AMIDE; MAGNESIUM; NITRILE; REAGENT; TERTIARY AMINE; TRIETHYLAMINE;

EID: 33750743697     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.09.087     Document Type: Article
Times cited : (17)

References (76)
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    • For recent examples of the use of the Bruylants reaction and its variations in synthesis, see:
  • 29
    • 33750688916 scopus 로고    scopus 로고
    • note
    • This is in marked contrast with the vast number of examples of non-racemic aminonitriles which contain two or more stereogenic centres. For some illustrations, see Ref. 3.
  • 31
    • 33750720706 scopus 로고    scopus 로고
    • Hylton, T. A.; Shenton, F. L. U.S. Patent 4,072,698, 1978;
  • 32
    • 25044469994 scopus 로고
    • Chem. Abstr. 88 (1978) 152276
    • (1978) Chem. Abstr. , vol.88 , pp. 152276
  • 33
    • 33750724193 scopus 로고    scopus 로고
    • Matthews, G. French Patent 2141354, 1973;
  • 34
    • 25044470255 scopus 로고
    • Chem. Abstr. 79 (1973) 42210
    • (1973) Chem. Abstr. , vol.79 , pp. 42210
  • 38
    • 33750714136 scopus 로고    scopus 로고
    • For reviews, see:
  • 40
  • 41
    • 33750691730 scopus 로고    scopus 로고
    • Schmalz H.-G., and Wirth T. (Eds), Wiley-VCH, Weinheim
    • Yet L. In: Schmalz H.-G., and Wirth T. (Eds). Organic Synthesis Highlights V (2003), Wiley-VCH, Weinheim 187-193
    • (2003) Organic Synthesis Highlights V , pp. 187-193
    • Yet, L.1
  • 43
    • 0034624418 scopus 로고    scopus 로고
    • An example of a one-pot three-component enantioselective Strecker reaction has been described, but the amine involved is an aniline, which therefore gives an N-monosubstituted aminonitrile, see:
    • An example of a one-pot three-component enantioselective Strecker reaction has been described, but the amine involved is an aniline, which therefore gives an N-monosubstituted aminonitrile, see:. Ishitani H., Komiyama S., Hasegawa Y., and Kobayashi S. J. Am. Chem. Soc. 122 (2000) 762-766
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 762-766
    • Ishitani, H.1    Komiyama, S.2    Hasegawa, Y.3    Kobayashi, S.4
  • 61
    • 33750719703 scopus 로고    scopus 로고
    • 3 or TFAA, apparently with total diastereoisomeric control, see:
  • 64
    • 33750733349 scopus 로고    scopus 로고
    • Compounds 2 are available commercially, although they can be expensive. As an alternative they can be prepared from the corresponding aminoacids using standard operations, see:
  • 71
    • 33750689932 scopus 로고    scopus 로고
    • note
    • Occasionally, the crude isolate had a small but non-zero optical rotation. This is explained by the presence of traces of the chiral carboxamide 3, carried through with the aminonitrile 1; the carboxamides are apparently not transformed in the Bruylants conditions. In such cases, the presence of the carboxamide was confirmed by GLC analysis of the crude Bruylants reaction product mixture.
  • 73
    • 84989478191 scopus 로고
    • We are aware of only one description of a series of Bruylants reactions which appear to have been carried out using 1.1 equiv of Grignard reagents. The substrates were α-secondary allylic α-aminonitriles and reported yields of amines averaged around 60%, see:
    • We are aware of only one description of a series of Bruylants reactions which appear to have been carried out using 1.1 equiv of Grignard reagents. The substrates were α-secondary allylic α-aminonitriles and reported yields of amines averaged around 60%, see:. Ahlbrecht H., and Dollinger H. Synthesis (1985) 743-748
    • (1985) Synthesis , pp. 743-748
    • Ahlbrecht, H.1    Dollinger, H.2
  • 75
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    • Wilkinson G., Stone F.G.A., and Abel E.W. (Eds), Pergamon, Oxford
    • Lindsell W.E. In: Wilkinson G., Stone F.G.A., and Abel E.W. (Eds). Comprehensive Organometallic Chemistry II Vol. 1 (1995), Pergamon, Oxford 57-127
    • (1995) Comprehensive Organometallic Chemistry II , vol.1 , pp. 57-127
    • Lindsell, W.E.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.