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Volumn 7, Issue 11, 2001, Pages 2435-2448

endo-selective intramolecular Pauson-Khand reactions of γ-oxygenated-α,β-unsaturated phenylsulfones

Author keywords

Allylic compounds; Enynes; Pauson Khand reaction; Stereoselectivity; Sulfones

Indexed keywords

CONDENSATION REACTIONS; OLEFINS; STEREOCHEMISTRY;

EID: 0035354751     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20010601)7:11<2435::AID-CHEM24350>3.0.CO;2-O     Document Type: Article
Times cited : (28)

References (70)
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    • For reviews on the Pauson-Khand reaction, see: a) K. M. Brummond, J. L. Kent, Tetrahedron 2000, 56, 3263;
    • (2000) Tetrahedron , vol.56 , pp. 3263
    • Brummond, K.M.1    Kent, J.L.2
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    • (Eds.: E. W. Abel, F. G. A. Stone, G. Wilkinson), Elsevier, New York
    • g) N. E. Schore, in Comprehensive Organometallic Chemistry II, Vol. 12 (Eds.: E. W. Abel, F. G. A. Stone, G. Wilkinson), Elsevier, New York, 1995, p. 703;
    • (1995) Comprehensive Organometallic Chemistry II, Vol. 12 , vol.12 , pp. 703
    • Schore, N.E.1
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    • (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford
    • i) N. E. Schore in Comprehensive Organic Synthesis, Vol. 5 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, pp. 1037;
    • (1991) Comprehensive Organic Synthesis, Vol. 5 , vol.5 , pp. 1037
    • Schore, N.E.1
  • 30
    • 0034613217 scopus 로고    scopus 로고
    • For other examples of exo selectivity in PK cyclizations of enynes substituted at allylic or propargylic positions, see: a) C. Mukai, H. Sonobe, J. S. Kim, M. Hanoka, J. Org. Chem. 2000, 65, 6654;
    • (2000) J. Org. Chem. , vol.65 , pp. 6654
    • Mukai, C.1    Sonobe, H.2    Kim, J.S.3    Hanoka, M.4
  • 40
    • 0001191177 scopus 로고
    • It has been known since the pioneering studies of Pauson and Khand that the reaction of alkyne dicobalt hexacarbonyl complexes with alkenes bearing electron-withdrawing groups (such as ethyl acrylate, acrylonitrile, methylvinylketone or divinyldisulfone) resulted predominantly in 1,3-dienes instead of the corresponding cyclopentenones. This behavior has been explained by the postulation that in these cases the cobaltacycle intermediate undergoes β-H elimination and formation of a conjugated alkene more rapidly than it does carbonyl insertion. See, for example: a) W. A. Smit, A. S. Gybin, A. S. Shashkov, Y. T. Strychkov, L. G. Kizmina, G. S. Mikaelian, R. Caple, E. D. Swanson, Tetrahedron Lett. 1986, 27, 1241;
    • (1986) Tetrahedron Lett. , vol.27 , pp. 1241
    • Smit, W.A.1    Gybin, A.S.2    Shashkov, A.S.3    Strychkov, Y.T.4    Kizmina, L.G.5    Mikaelian, G.S.6    Caple, R.7    Swanson, E.D.8
  • 51
    • 0344117715 scopus 로고    scopus 로고
    • To the best of our knowledge, the only reported examples of endo selectivity in a PK reaction of an allylic substituted enyne concerns some specific 3,4-disubstituted enynes, see: a) C. Mukai, J. S. Kim, H. Sonobe, M. Hanaoka, J. Org. Chem. 1999, 64, 6822;
    • (1999) J. Org. Chem. , vol.64 , pp. 6822
    • Mukai, C.1    Kim, J.S.2    Sonobe, H.3    Hanaoka, M.4
  • 55
    • 33751500117 scopus 로고
    • For the synthesis of γ-hydroxy-α,β-unsaturated sulfones by condensation of aldehydes with sulfinyl sulfonyl methanes, see: a) B. M. Trost, T. A. Greese, J. Org. Chem. 1991, 56, 3189;
    • (1991) J. Org. Chem. , vol.56 , pp. 3189
    • Trost, B.M.1    Greese, T.A.2
  • 58
    • 20444497278 scopus 로고    scopus 로고
    • note
    • Crystallographic data (excluding structure factors) for the structure endo-9c reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-141942. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: (+44) 1223-336-033; e-mail: deposit@ccdc.cam. ac.uk)..
  • 59
    • 0000354667 scopus 로고
    • 2, RT; j) nBuLi, THF, 0°C; k) 5M HCl, MeOH, RT; l) NaOH, propargyl bromide, RT. See also: a) W. Oppolzer, J. Z. Xu, C. Stone, Helv. Chim. Acta 1991, 74, 465;
    • (1991) Helv. Chim. Acta , vol.74 , pp. 465
    • Oppolzer, W.1    Xu, J.Z.2    Stone, C.3
  • 66
    • 0025068753 scopus 로고
    • For another method for the enantioselective preparation of γ-hydroxy-α,β-unsaturated sulfones, see: E. J. Corey, R. K. Bakshi, Tetrahedron Lett. 1990, 31, 611.
    • (1990) Tetrahedron Lett. , vol.31 , pp. 611
    • Corey, E.J.1    Bakshi, R.K.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.