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Volumn 46, Issue 8, 2010, Pages 1281-1283

Mukaiyama aldol addition to α-chloro-substituted aldehydes. Origin of the unexpected syn selectivity

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; BORON; CARBONYL DERIVATIVE; LEWIS ACID; NUCLEOPHILE; PENTANE; SILANE DERIVATIVE;

EID: 76349096927     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b922954j     Document Type: Article
Times cited : (26)

References (33)
  • 1
    • 0003417469 scopus 로고
    • ed., B. M. Trost and I. Fleming, Pergamon, New York
    • Comprehensive Organic Synthesis, ed., B. M. Trost, and, I. Fleming, Pergamon, New York, 1991, vol. 2
    • (1991) Comprehensive Organic Synthesis
  • 2
    • 0003495415 scopus 로고
    • ed. G. Helmchen, R. W. Hoffmann, J. Mulzer and E. Schaumann, Thieme, Stuttgart
    • A. Houben-Weyl, Methods of Organic Chemistry, ed., G. Helmchen, R. W. Hoffmann, J. Mulzer, and, E. Schaumann, Thieme, Stuttgart, 1995, vol. E 21b, ch. 1.3
    • (1995) Methods of Organic Chemistry
    • Houben-Weyl, A.1
  • 3
    • 0000584420 scopus 로고
    • ed., J. D. Morrison, Academic, Orlando
    • C. H. Heathcock, in Asymmetric Synthesis, ed., J. D. Morrison, Academic, Orlando, 1984, vol. 3, pp. 111-212
    • (1984) Asymmetric Synthesis , pp. 111-212
    • Heathcock In, C.H.1
  • 7
    • 0003445429 scopus 로고    scopus 로고
    • ed., E. N. Jacobsen, A. Pflatz and H. Yamamoto, Springer-Verlag, Heidelberg
    • E. M. Carreira, in Comprehensive Asymmetric Catalysis, ed., E. N. Jacobsen, A. Pflatz, and, H. Yamamoto, Springer-Verlag, Heidelberg, 1999, vol. 3, ch. 29
    • (1999) Comprehensive Asymmetric Catalysis
    • Carreira In, E.M.1
  • 19
    • 33644959351 scopus 로고    scopus 로고
    • For stereochemical assignments of compounds 1-4, 10-15 and 19-21, see the ESI
    • For stereochemical assignments of compounds 1-4, 10-15 and 19-21, see the ESI V. J. Cee C. J. Cramer D. A. Evans J. Am. Chem. Soc. 2006 128 2920 2930
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 2920-2930
    • Cee, V.J.1    Cramer, C.J.2    Evans, D.A.3
  • 27
    • 76349119310 scopus 로고    scopus 로고
    • Note
    • -1 higher in energy than the most stable conformer.
  • 31
    • 76349113003 scopus 로고    scopus 로고
    • Note
    • The aldehyde rotamer with the α-chloro substituent perpendicular to the incoming nucleophile is judged less likely since it would result in a destabilizing steric interaction between R′ and one substituent on the enol silane (R or OTMS)
  • 32
    • 0031018562 scopus 로고    scopus 로고
    • For an example where a TS structure similar to D has been invoked to rationalize the stereochemical outcome in the addition to an α-silyloxy aldehyde, see
    • For an example where a TS structure similar to D has been invoked to rationalize the stereochemical outcome in the addition to an α-silyloxy aldehyde, see: A. B. Smith, III S. M. Condon J. A. McCauley J. L. Leazer, Jr. J. W. Leahy R. E. Maleczka, Jr. J. Am. Chem. Soc. 1997 119 947 961
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 947-961
    • Smith Iii, A.B.1    Condon, S.M.2    McCauley, J.A.3    Leazer Jr., J.L.4    Leahy, J.W.5    Maleczka Jr., R.E.6
  • 33
    • 76349114561 scopus 로고    scopus 로고
    • Note
    • Theoretical studies suggest that α-amino substituted aldehydes react through PFA TS structures in the boron aldol reaction. See ref. 8


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.