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Volumn 353, Issue 11-12, 2011, Pages 2022-2036

Diastereoselective nucleophilic addition to aldehydes with polar α- And α,β-substituents

Author keywords

aldol reaction; allylation; diastereoselectivity; induction model

Indexed keywords


EID: 80052019661     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201100173     Document Type: Article
Times cited : (18)

References (53)
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    • Similar observations have also been made by other groups. See, for example
    • Angew. Chem. Int. Ed. 2003, 42, 1761-1765. Similar observations have also been made by other groups. See, for example
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    • For discussions of the role of syn-pentane interactions in aldol reactions, see
    • For discussions of the role of syn-pentane interactions in aldol reactions, see
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    • 80051988166 scopus 로고    scopus 로고
    • For the synthesis of aldehydes 1, 2, 4, 5 and 28-37 see Supporting Information.
    • For the synthesis of aldehydes 1, 2, 4, 5 and 28-37 see Supporting Information.
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    • [8b], footnote 31.
    • [8b], footnote 31.
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    • The aldehyde rotamer having the α-chloro substituent perpendicular to the C=O moiety (anti-PFA TS) 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).
    • The aldehyde rotamer having the α-chloro substituent perpendicular to the C=O moiety (anti-PFA TS) 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).
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    • [7]
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    • For an example where a TS structure similar to J 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 J 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
    • Iii, A.B.S.1    Condon, S.M.2    McCauley, J.A.3    Leazer Jr., J.L.4    Leahy, J.W.5    Maleczka Jr., R.E.6
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    • For determination of the relative stereochemistry, see Supporting Information.
    • For determination of the relative stereochemistry, see Supporting Information.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.