메뉴 건너뛰기




Volumn 16, Issue 32, 2010, Pages 9741-9745

Benzylic boron reagents behaving as allylic boron reagents towards aldehydes: A new asymmetric reaction leading to homoallylic alcohols with concomitant dearomatisation

Author keywords

Allylboration; Asymmetric catalysis; Borylation; Dearomatization; Lithiation

Indexed keywords

ALLYLBORATION; ASYMMETRIC CATALYSIS; BORYLATION; DEAROMATIZATION; LITHIATION;

EID: 77955884643     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201001174     Document Type: Article
Times cited : (12)

References (50)
  • 3
    • 0042291889 scopus 로고    scopus 로고
    • (Ed.: D. Astruc), Wiley-VCH, Weinheim
    • b) S. Quideau in Modern Arene Chemistry (Ed.: D. Astruc), Wiley-VCH, Weinheim, 2002, pp. 539 - 573
    • (2002) Modern Arene Chemistry , pp. 539-573
    • Quideau, S.1
  • 27
    • 70350442360 scopus 로고    scopus 로고
    • The trifluoroborate salts were prepared from the boronic esters through a modification of the Vedejs protocol b) V. Bagutski, A. Ros, V. K. Aggarwal, Tetrahedron 2009, 65, 9956.
    • (2009) Tetrahedron , vol.65 , pp. 9956
    • Bagutski, V.1    Ros, A.2    Aggarwal, V.K.3
  • 28
    • 57649120956 scopus 로고    scopus 로고
    • and the secondary boronic esters were prepared by the lithiation-borylation reaction of primary carabamates
    • The tertiary boronic esters were prepared by the lithiation-borylation reaction of a secondary carbamate c) J. L. Stymiest, V. Bagutski, R. M. French, V. K. Aggarwal, Nature 2008, 456, 778, and the secondary boronic esters were prepared by the lithiation-borylation reaction of primary carabamates
    • (2008) Nature , vol.456 , pp. 778
    • Stymiest, J.L.1    Bagutski, V.2    French, R.M.3    Aggarwal, V.K.4
  • 35
    • 77955884860 scopus 로고    scopus 로고
    • Oxidation of the 3:1 mixture of isomers gave a 3:1 mixture of ketones indicating that the diastereomeric mixture was due to E and Z alkene isomers. NOE studies confirmed the ZIE products
    • Oxidation of the 3:1 mixture of isomers gave a 3:1 mixture of ketones indicating that the diastereomeric mixture was due to E and Z alkene isomers. NOE studies confirmed the ZIE products.
  • 36
    • 0000554723 scopus 로고    scopus 로고
    • (Ed.: J. Otera). Wiley-VCH, Weinheim. Chapter 10
    • For reviews on allylboration of aldehydes, see: a) S. E. Denmark, N. G. Almstead in Modern Carbonyl Chemistry (Ed.: J. Otera). Wiley-VCH, Weinheim. 2000, Chapter 10. p. 299:
    • (2000) Modern Carbonyl Chemistry , pp. 299
    • Denmark, S.E.1    Almstead, N.G.2
  • 37
  • 38
    • 34447526812 scopus 로고    scopus 로고
    • (Ed.: S. E. Denmark). Wiley. New York
    • c) H. Lachance. D.G. Hall in Organic Reactions, Vol. 73 (Ed.: S. E. Denmark). Wiley. New York, 2008
    • (2008) Organic Reactions , vol.73
    • Lachance, H.1    Hall, D.G.2
  • 40
    • 0000094579 scopus 로고    scopus 로고
    • 4th ed. (Eds.: G. Helmchen. R. W. Hoffman. J. Mulzer. E. Schaumann), Thieme, Stuttgart
    • e) W. R. Roush in Stereoselective Synthesis: Methods of Organic Synthesis, Vol. 3, 4th ed. (Eds.: G. Helmchen. R. W. Hoffman. J. Mulzer. E. Schaumann), Thieme, Stuttgart. 1996, p. 1410
    • (1996) Stereoselective Synthesis: Methods of Organic Synthesis , vol.3 , pp. 1410
    • Roush, W.R.1
  • 42
    • 3142676522 scopus 로고    scopus 로고
    • For examples of reactions of allyl trifluoroborate salts with aldehydes, see g) S.-W. Li, R. A. Batey. Chem. Commun. 2004, 1382
    • (2004) Chem. Commun. , pp. 1382
    • Li, S.-W.1    Batey, R.A.2
  • 45
    • 77955889694 scopus 로고    scopus 로고
    • X-ray analyses were achieved on the major enantiomer of the (Z)-p-nitrobenzaldehyde adduct and the major and minor enantiomers of the £ benzaldehyde adducts which were more readily separable. See the Supporting Information
    • X-ray analyses were achieved on the major enantiomer of the (Z)-p-nitrobenzaldehyde adduct and the major and minor enantiomers of the £ benzaldehyde adducts which were more readily separable. See the Supporting Information.
  • 46
    • 0001055223 scopus 로고
    • A similar reactivity through an open TS was invoked in the reactions of lithium allylic borate complexes with aldehydes. See: Y. Yamamoto, H. Yalagai, K. Maruyama, J. Am. Chem. Soc. 1981, 103, 1969.
    • (1981) J. Am. Chem. Soc. , vol.103 , pp. 1969
    • Yamamoto, Y.1    Yalagai, H.2    Maruyama, K.3
  • 47
    • 4344657754 scopus 로고    scopus 로고
    • A primary 4-methoxybenzyl Grignard reagent has also been reported to react with certain aldehydes through the aromatic ring with concomitant dearomatisation. See: a) G. A. Kraus, I. Kim, S. Kesavan, Tetrahedron Lett. 2004, 45, 6839
    • (2004) Tetrahedron Lett. , vol.45 , pp. 6839
    • Kraus, G.A.1    Kim, I.2    Kesavan, S.3
  • 48
    • 77955889038 scopus 로고    scopus 로고
    • For Pd-catalysed allylative dearomatisation of benzylic chlorides see reference [3i]
    • b) For Pd-catalysed allylative dearomatisation of benzylic chlorides see reference [3i]
  • 50
    • 77955879153 scopus 로고    scopus 로고
    • The primary p-methoxybenzyl trifluoroborate salt was also tested and gave the corresponding homoallylic alcohol related to 2 in 36% yield (unoptimized). See the Supporting Information for details
    • The primary p-methoxybenzyl trifluoroborate salt was also tested and gave the corresponding homoallylic alcohol related to 2 in 36% yield (unoptimized). See the Supporting Information for details.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.