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Volumn , Issue , 2016, Pages 2046-2060

Recent Developments in the Chiral Brønsted Acid-catalyzed Allylboration Reaction with Polyfunctionalized Substrates

Author keywords

allylic compounds; asymmetric allylboration; chiral Br nsted acid catalysis; density functional calculations; diversity oriented synthesis

Indexed keywords


EID: 84981724878     PISSN: 15278999     EISSN: 15280691     Source Type: Journal    
DOI: 10.1002/tcr.201600069     Document Type: Article
Times cited : (19)

References (100)
  • 1
    • 84981707359 scopus 로고    scopus 로고
    • For recent reviews on asymmetric allylation reactions, see
    • For recent reviews on asymmetric allylation reactions, see:
  • 11
    • 0002446724 scopus 로고
    • in, Vol, (Ed., B. M. Trost, Pergamon Press, Oxford, p
    • (h) W. R. Roush, in: Comprehensive Organic Synthesis, Vol. 2, (Ed.: B. M. Trost), Pergamon Press, Oxford, 1991, p. 1.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 1
    • Roush, W.R.1
  • 18
  • 30
    • 84981728870 scopus 로고    scopus 로고
    • For seminal contributions on chiral phosphoric acid catalysis, see
    • For seminal contributions on chiral phosphoric acid catalysis, see:
  • 33
    • 84981713551 scopus 로고    scopus 로고
    • For reviews on chiral phosphoric acid catalysis, see
    • For reviews on chiral phosphoric acid catalysis, see:
  • 43
    • 33845477631 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed, 2006,, 45, 3909
    • (j) S. J. Connon, Angew. Chem. 2006, 118, 4013; Angew. Chem. Int. Ed. 2006, 45, 3909.
    • (2006) Angew. Chem. , vol.118 , pp. 4013
    • Connon, S.J.1
  • 45
    • 84863011869 scopus 로고    scopus 로고
    • One year later, the same authors revisited their own results showing that the activation of the pseudo-equatorial oxygen of the boronate leads to the formation of the minor enantiomer
    • (a) P. Jain, H. Wang, K. N. Houk, J. C. Antilla, Angew. Chem. Int. Ed. 2012, 51, 1391. One year later, the same authors revisited their own results showing that the activation of the pseudo-equatorial oxygen of the boronate leads to the formation of the minor enantiomer:
    • (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 1391
    • Jain, P.1    Wang, H.2    Houk, K.N.3    Antilla, J.C.4
  • 48
    • 84981748515 scopus 로고    scopus 로고
    • For modifications and applications of the original conditions, see
    • For modifications and applications of the original conditions, see:
  • 63
  • 64
    • 84981709776 scopus 로고    scopus 로고
    • For excellent reviews on the classification of tandem catalysis, see
    • For excellent reviews on the classification of tandem catalysis, see:
  • 67
    • 84981740625 scopus 로고    scopus 로고
    • For selected examples of relay catalysis using chiral phosphoric acid/transition metal binary systems, see
    • For selected examples of relay catalysis using chiral phosphoric acid/transition metal binary systems, see:
  • 69
    • 84868565292 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed, 2012,, 51, 2093;
    • (b) M. Terada, Y. Toda, Angew. Chem. 2012, 124, 2135; Angew. Chem. Int. Ed. 2012, 51, 2093;
    • (2012) Angew. Chem. , vol.124 , pp. 2135
    • Terada, M.1    Toda, Y.2
  • 75
    • 84981704828 scopus 로고    scopus 로고
    • For a cross-metathesis/intramolecular aza-Michael process, see
    • For a cross-metathesis/intramolecular aza-Michael process, see:
  • 76
    • 79958250843 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed, 2010,, 49, 8666. For a cross-metathesis/intramolecular Friedel–Crafts alkylation sequence, see
    • (a) Q. Cai, C. Zheng, S.-L. You, Angew. Chem. 2010, 122, 8848; Angew. Chem. Int. Ed. 2010, 49, 8666. For a cross-metathesis/intramolecular Friedel–Crafts alkylation sequence, see:
    • (2010) Angew. Chem. , vol.122 , pp. 8848
    • Cai, Q.1    Zheng, C.2    You, S.-L.3
  • 77
    • 77149175767 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed, 2009,, 48, 7428
    • (b) Q. Cai, Z. A. Zhao, S.-L. You, Angew. Chem. 2009, 121, 7564; Angew. Chem. Int. Ed. 2009, 48, 7428.
    • (2009) Angew. Chem. , vol.121 , pp. 7564
    • Cai, Q.1    Zhao, Z.A.2    You, S.-L.3
  • 80
    • 84981707257 scopus 로고    scopus 로고
    • –ΔG values are used in order to obtain positive numbers
    • –ΔG values are used in order to obtain positive numbers.
  • 81
    • 84981714122 scopus 로고    scopus 로고
    • Estimated based on the small increase of the A-value from methyl (1.74 kcal mol,) to ethyl (1.79 kcal mol
    • −1).
  • 82
    • 84981714568 scopus 로고
    • No A-value for TIPS has been found in the literature. However, the relative deprotection rates towards catalyzed solvolysis (expressed as 1/k,) for TMSvs. TIPS (700,000) protected alcohols gives a rough idea of the much higher steric hinderance of the latter silyl group. See, Protecting Groups, Thieme,, p
    • rel) for TMS (1) vs. TIPS (700,000) protected alcohols gives a rough idea of the much higher steric hinderance of the latter silyl group. See: P. J. Kocienski, Protecting Groups, Thieme, 1994, p. 189.
    • (1994) , Issue.1 , pp. 189
    • Kocienski, P.J.1
  • 84
    • 84981728902 scopus 로고    scopus 로고
    • O hydrogen bond interactions of this type have been shown to play a crucial role in many asymmetric reactions
    • Formyl CH•••O hydrogen bond interactions of this type have been shown to play a crucial role in many asymmetric reactions:
    • Formyl, C.H.1
  • 90
    • 84981748540 scopus 로고    scopus 로고
    • For seminal publications on chiral Brønsted acid catalysis, see
    • For seminal publications on chiral Brønsted acid catalysis, see:
  • 93
    • 84981713577 scopus 로고    scopus 로고
    • For recent reviews on chiral Brønsted acid catalysis, see
    • For recent reviews on chiral Brønsted acid catalysis, see:
  • 100
    • 84873979724 scopus 로고    scopus 로고
    • Recently, the reverse reaction sequence (electrophilic allylic fluorination/allylboration) using isomeric γ-silylvinylboronates has been described
    • Recently, the reverse reaction sequence (electrophilic allylic fluorination/allylboration) using isomeric γ-silylvinylboronates has been described: A. Mace, F. Tripoteau, Q. Zhao, E. Gayon, E. Vrancken, J.-M. Campagne, B. Carboni, Org. Lett. 2013, 15, 906.
    • (2013) Org. Lett. , vol.15 , pp. 906
    • Mace, A.1    Tripoteau, F.2    Zhao, Q.3    Gayon, E.4    Vrancken, E.5    Campagne, J.-M.6    Carboni, B.7


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.