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Volumn 76, Issue 11, 2003, Pages 2183-2189

Unusual Carbonyl Differentiation in the Lewis Acid-Catalyzed Allylation of Aldehydes with Tetraallyltin. Applications to Parallel Recognition and Shotgun Process

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYLATION; CATALYSIS; CATALYSTS; SUBSTRATES;

EID: 0344234224     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.76.2183     Document Type: Article
Times cited : (6)

References (41)
  • 1
    • 0003913629 scopus 로고    scopus 로고
    • ed by J. Otera, Wiley-VCH, Weinheim
    • For a most recent review, see: S. Saito and H. Yamamoto, "Modern Carbonyl Chemistry," ed by J. Otera, Wiley-VCH, Weinheim (2000), p. 33.
    • (2000) Modern Carbonyl Chemistry , pp. 33
    • Saito, S.1    Yamamoto, H.2
  • 2
    • 1542513031 scopus 로고    scopus 로고
    • The steric effects by bulky Lewis acids are also effective for the selective reaction; see: K. Maruoka, S. Saito, and H. Yamamoto, Synlett, 1994, 439.
    • Synlett , vol.1994 , pp. 439
    • Maruoka, K.1    Saito, S.2    Yamamoto, H.3
  • 5
    • 0003831823 scopus 로고    scopus 로고
    • Organotin triflates and perchlorates; see: a) J. Chen and J. Otera, Synlett, 1997, 29.
    • Synlett , vol.1997 , pp. 29
    • Chen, J.1    Otera, J.2
  • 32
    • 0344456892 scopus 로고    scopus 로고
    • note
    • It is not clear at the moment that TMSOTf works as a typical Lewis acid in its innate form. The reaction with tetraallyltin may occur to form allyltrimethlysilane and allyltin triflates.
  • 34
    • 0344025746 scopus 로고    scopus 로고
    • note
    • Mori et al. reported one such case where alkanal reacted with TMSCN whereas benzaldehyde with ketene silyl acetal, respectively.6 In this case, the selectivity of the nucleophiles towards alkanal and ketene silyl acetal is perfect: in the competition reactions towards a mixture of alkanal and benzealdehyde, TMSCN reacted with alkanal and ketene silyl acetal with benzaldehyde exclusively. Accordingly, the absence of the crossed-reaction products is taken as a matter of course.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.