메뉴 건너뛰기




Volumn 2, Issue 9, 1996, Pages 1077-1084

TiIV-BINOLate-catalyzed highly enantioselective additions of β-substituted allylstannanes to aldehydes

Author keywords

Allylstannanes; Asymmetric allylations; C C bond formation; Catalysis; Homoallylic alcohols

Indexed keywords

ALLYLSTANNANES; ALLYLTRIBUTYLSTANNANE; ANALOGOUS REACTIONS; ASYMMETRIC ALLYLATIONS; C-C BOND FORMATION; ENANTIOSELECTIVE ADDITION; HOMOALLYL ALCOHOL; HOMOALLYLIC ALCOHOL;

EID: 84891301252     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.19960020907     Document Type: Article
Times cited : (69)

References (47)
  • 4
    • 0001432032 scopus 로고
    • cf. also the literature cited in
    • c) cf. also the literature cited in S. E. Denmark, B. R. Henke, J. Am. Chem. Soc. 1991, 113, 2177-2194.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 2177-2194
    • Denmark, S.E.1    Henke, B.R.2
  • 6
    • 0001134408 scopus 로고
    • Review
    • Review: T. Bach, Angew. Chem. 1994, 106, 433-435;
    • (1994) Angew. Chem. , vol.106 , pp. 433-435
    • Bach, T.1
  • 13
    • 33751386025 scopus 로고
    • In this paper the absolute configurations of the addition products are drawn with a configuration opposite to the entries in the table
    • G. E. Keck, D. Krishnamurthy, M. C. Grier, J. Org. Chem. 1993, 58, 6543-6544. In this paper the absolute configurations of the addition products are drawn with a configuration opposite to the entries in the table.
    • (1993) J. Org. Chem. , vol.58 , pp. 6543-6544
    • Keck, G.E.1    Krishnamurthy, D.2    Grier, M.C.3
  • 22
    • 84891335287 scopus 로고    scopus 로고
    • S. Weigand, Diplomarbeit, Universität Göttingen, 1994
    • S. Weigand, Diplomarbeit, Universität Göttingen, 1994.
  • 23
    • 0141442424 scopus 로고
    • The enantioselective addition of a chiral (β-bromoallyl)boronate to aldehydes was described by
    • The enantioselective addition of a chiral (β-bromoallyl)boronate to aldehydes was described by S. Hara, Y. Yamamoto, A. Fujita, A. Suzuki, Synlett 1994, 639-640.
    • (1994) Synlett , pp. 639-640
    • Hara, S.1    Yamamoto, Y.2    Fujita, A.3    Suzuki, A.4
  • 24
    • 0028906005 scopus 로고
    • Stereoselective additions of a β-(1-methoxyethylated) allyltributylstannane to aldehydes were described by However, this reagent is conceptually unrelated to the reagents 1-9 of Scheme 1
    • Stereoselective additions of a β-(1-methoxyethylated) allyltributylstannane to aldehydes were described by Y. Nishigaishi, H. Kuramoto, A. Takuwa, Tetrahedron Lett. 1995, 36, 3353-3356. However, this reagent is conceptually unrelated to the reagents 1-9 of Scheme 1.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 3353-3356
    • Nishigaishi, Y.1    Kuramoto, H.2    Takuwa, A.3
  • 27
    • 0000207239 scopus 로고    scopus 로고
    • 2, (R)-BINOL, and 4 Å molecular sieves were used to induce enantioselectivity in inverse electron demand Diels-Alder reactions between pyrone-3-carboxylates and enol ethers. The critical dependence of the enantiomeric excesses on the nature of the molecular sieves (water content, trace elements) was investigated at length. Hence, in retrospect, our failure to reproduce Keck's best results by his method may have been caused by differences in the molecular sieves. Since molecular sieves are omitted in our protocol, the necessity of exploring which molecular sieves give best results is circumvented
    • 2, (R)-BINOL, and 4 Å molecular sieves were used to induce enantioselectivity in inverse electron demand Diels-Alder reactions between pyrone-3-carboxylates and enol ethers. The critical dependence of the enantiomeric excesses on the nature of the molecular sieves (water content, trace elements) was investigated at length. Hence, in retrospect, our failure to reproduce Keck's best results by his method may have been caused by differences in the molecular sieves. Since molecular sieves are omitted in our protocol, the necessity of exploring which molecular sieves give best results is circumvented.
    • (1996) J. Org. Chem. , vol.61 , pp. 671-676
    • Posner, G.H.1    Dai, H.2    Bull, D.S.3    Lee, J.-K.4    Eydoux, F.5    Ishihara, Y.6    Welsh, W.7    Pryov, N.8    Petr Jr., S.9
  • 28
    • 0029916773 scopus 로고    scopus 로고
    • Preparation of β-substitued allylstannanes
    • Preparation of β-substitued allylstannanes: S. Weigand, R. Brückner, Synthesis 1996, 475-483.
    • (1996) Synthesis , pp. 475-483
    • Weigand, S.1    Brückner, R.2
  • 37
    • 84891326053 scopus 로고
    • Dissertation, Universität Würzburg
    • H. Priepke, Dissertation, Universität Würzburg, 1993.
    • (1993)
    • Priepke, H.1
  • 39
    • 84891304589 scopus 로고    scopus 로고
    • unpublished results
    • S. Weigand, unpublished results.
    • Weigand, S.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.