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Volumn 132, Issue 15, 2010, Pages 5354-5356

Super silyl stereo-directing groups for complete 1,5-Syn and -anti stereoselectivities in the aldol reactions of β-siloxy methyl ketones with aldehydes

Author keywords

[No Author keywords available]

Indexed keywords

ALDOL REACTIONS; DIASTEREOSELECTIVITIES; METHYL KETONES; SILYL GROUP;

EID: 77951029880     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja101076q     Document Type: Article
Times cited : (49)

References (63)
  • 1
    • 0001527822 scopus 로고
    • For reviews of polyketides, see
    • For reviews of polyketides, see: Rychnovsky, S. D. Chem. Rev. 1995, 95, 2021
    • (1995) Chem. Rev. , vol.95 , pp. 2021
    • Rychnovsky, S.D.1
  • 9
    • 30744432615 scopus 로고    scopus 로고
    • For reviews of 1,5-asymmetric induction in the aldol reaction, see
    • For reviews of 1,5-asymmetric induction in the aldol reaction, see: Yeung, K. and Paterson, I. Chem. Rev 2005, 105, 4237
    • (2005) Chem. Rev , vol.105 , pp. 4237
    • Yeung, K.1    Paterson, I.2
  • 45
    • 33749011942 scopus 로고    scopus 로고
    • Computational studies
    • Computational studies: Paton, R. S. and Goodman, J. M. Org. Lett. 2006, 8, 4299
    • (2006) Org. Lett. , vol.8 , pp. 4299
    • Paton, R.S.1    Goodman, J.M.2
  • 53
    • 5244345331 scopus 로고
    • Tris(triethylsilyl)silane can easily be prepared from chlorotriethylsilane and trichlorosilane. See
    • Tris(triethylsilyl)silane can easily be prepared from chlorotriethylsilane and trichlorosilane. See: Bürger, H. and Kilian, W. J. Organomet. Chem. 1971, 26, 47
    • (1971) J. Organomet. Chem. , vol.26 , pp. 47
    • Bürger, H.1    Kilian, W.2
  • 56
    • 77951075114 scopus 로고    scopus 로고
    • The use of the dicyclohexylboron enolate of substrate 1a with pivalaldehyde gave a slightly lower anti selectivity (85:15)
    • The use of the dicyclohexylboron enolate of substrate 1a with pivalaldehyde gave a slightly lower anti selectivity (85:15).
  • 57
    • 77951034319 scopus 로고    scopus 로고
    • The reduction of anti - 4a also gave a syn/anti product mixture in 89% yield with high selectivity (91:9)
    • The reduction of anti-4a also gave a syn/anti product mixture in 89% yield with high selectivity (91:9).
  • 61
    • 77951062766 scopus 로고    scopus 로고
    • 2/ i -PrCHO, and DIBAL-H gave low yields or low selectivities for anti / anti - 8
    • 2/ i -PrCHO, and DIBAL-H gave low yields or low selectivities for anti / anti-8.
  • 62
    • 77951083400 scopus 로고    scopus 로고
    • 3 gave the 1,3,5-syn/syn product as a single isomer. The relative configurations of products 5a, 7, and 8 were determined on the basis of the NMR spectra of these related compounds (see the Supporting Information for full details)
    • 3 gave the 1,3,5-syn/syn product as a single isomer. The relative configurations of products 5a, 7, and 8 were determined on the basis of the NMR spectra of these related compounds (see the Supporting Information for full details).
  • 63
    • 0032486158 scopus 로고    scopus 로고
    • For the synthesis of aldehyde 11, see:, For the synthesis of ketone 9, see ref 2b
    • For the synthesis of aldehyde 11, see: Botuha, C., Haddad, M., and Larcheveque, M. Tetrahedron: Asymmetry 1998, 9, 1929 For the synthesis of ketone 9, see ref 2b.
    • (1998) Tetrahedron: Asymmetry , vol.9 , pp. 1929
    • Botuha, C.1    Haddad, M.2    Larcheveque, M.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.