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Volumn 15, Issue 12, 2004, Pages 1909-1913

α-Amino acid-promoted asymmetric allylation of aldehydes with allylstannanes

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALDEHYDE; ALKANE DERIVATIVE; ALLYL COMPOUND; AMINO ACID DERIVATIVE; ASPARTIC ACID;

EID: 2942676874     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2004.04.036     Document Type: Article
Times cited : (32)

References (57)
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    • Yamamoto H. Weinheim: Wiley-VCH
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    • (2000) Lewis Acids in Organic Synthesis , vol.12
  • 21
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    • Recent examples of chiral Lewis acid-catalyzed asymmetric allylations:
    • Recent examples of chiral Lewis acid-catalyzed asymmetric allylations: Wadamoto M., Ozasa N., Yanagisawa A., Yamamoto H. J. Org. Chem. 68:2003;5593
    • (2003) J. Org. Chem. , vol.68 , pp. 5593
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  • 27
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    • Recent examples of chiral Lewis base-catalyzed asymmetric allylations:
    • Recent examples of chiral Lewis base-catalyzed asymmetric allylations: Denmark S.E., Fu J. Chem. Commun. 2003;167
    • (2003) Chem. Commun. , pp. 167
    • Denmark, S.E.1    Fu, J.2
  • 34
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    • Recent examples of catalytic asymmetric Nozaki-Hiyama reactions with chromium catalysts:
    • Recent examples of catalytic asymmetric Nozaki-Hiyama reactions with chromium catalysts: Suzuki T., Kinoshita A., Kawada H., Nakada M. Synlett. 2003;570
    • (2003) Synlett , pp. 570
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  • 39
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    • We have previously shown that tetraallyltin reacts with aldehydes in acidic aqueous media:
    • We have previously shown that tetraallyltin reacts with aldehydes in acidic aqueous media: Yanagisawa A., Inoue H., Morodome M., Yamamoto H. J. Am. Chem. Soc. 115:1993;10356
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 10356
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    • In the present reaction, an excess (2 equiv) of tetraallyltin is necessary to obtain a satisfactory isolated yield
    • Yanagisawa A., Morodome M., Nakashima H., Yamamoto H. Synlett. 1997;1309. In the present reaction, an excess (2 equiv) of tetraallyltin is necessary to obtain a satisfactory isolated yield
    • (1997) Synlett , pp. 1309
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  • 41
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    • note
    • Cyclohexanecarboxaldehyde, a bulky aliphatic aldehyde, showed a comparatively low reactivity (62% yield) under the same reaction conditions
  • 49
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    • For another method of preparation of the racemic compound, see:
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    • For a method of analytical resolution of the racemic compound, see:
    • For a method of analytical resolution of the racemic compound, see: Halterman R.L., Roush W.R., Hoong L.K. J. Org. Chem. 52:1987;1152
    • (1987) J. Org. Chem. , vol.52 , pp. 1152
    • Halterman, R.L.1    Roush, W.R.2    Hoong, L.K.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.