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Volumn , Issue 4, 2010, Pages 579-582

A novel asymmetric azaspirocyclisation using a Morita-Baylis-Hillman-type reaction

Author keywords

Asymmetric synthesis; Azaspirocyclisation; Diastereoselectivity; Morita Baylis Hillman type reaction; Spiro compounds

Indexed keywords

SPIRO COMPOUND;

EID: 77955400123     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1219210     Document Type: Article
Times cited : (11)

References (46)
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    • For a review on synthesis, see
    • (f) For a review on synthesis, see: Weinreb, S. M. Chem. Rev. 2006, 106, 2531.
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    • Weinreb, S.M.1
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  • 20
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    • The addition of dimethyl sulfide to cyclohexenone in the presence of TMSOTf is 1,4-selective and reversible. The silyloxysulfonium salt produced is thermally unstable above -40 °C. At -20 °C the equilibrium lies entirely on the side of the cyclohexenone
    • The addition of dimethyl sulfide to cyclohexenone in the presence of TMSOTf is 1,4-selective and reversible. The silyloxysulfonium salt produced is thermally unstable above -40 °C. At -20 °C the equilibrium lies entirely on the side of the cyclohexenone: (a) Kim, S.; Park, J. H.; Kim, Y. G.; Lee, J. M. J. Chem. Soc., Chem. Commun. 1993, 1188.
    • (1993) J. Chem. Soc., Chem. Commun. , pp. 1188
    • Kim, S.1    Park, J.H.2    Kim, Y.G.3    Lee, J.M.4
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    • 0033431540 scopus 로고    scopus 로고
    • For a review on stereochemistry of nucleophilic addition to aminals using this auxiliary, see
    • (l) For a review on stereochemistry of nucleophilic addition to aminals using this auxiliary, see: Husson, H. P.; Royer, J. Chem. Soc. Rev. 1999, 28, 383.
    • (1999) Chem. Soc. Rev. , vol.28 , pp. 383
    • Husson, H.P.1    Royer, J.2
  • 36
    • 0022517466 scopus 로고
    • The following Lewis acids and nucleophile combinations were screened for the MBH-type reaction without success: (a) HCl
    • The following Lewis acids and nucleophile combinations were screened for the MBH-type reaction without success: (a) HCl: Melching, K. H.; Hiemstra, H.; Klaver, W. J.; Speckamp, W. N. Tetrahedron Lett. 1986, 27, 4799.
    • (1986) Tetrahedron Lett. , vol.27 , pp. 4799
    • Melching, K.H.1    Hiemstra, H.2    Klaver, W.J.3    Speckamp, W.N.4
  • 40
    • 77955375351 scopus 로고    scopus 로고
    • We were not able to obtain crystals of the 5,5-spirocycle for analysis by X-ray diffraction, and we were unsuccessful in finding NOE correlations to assign its stereochemistry. The spirocentre stereochemistry is therefore not known in this case
    • We were not able to obtain crystals of the 5,5-spirocycle for analysis by X-ray diffraction, and we were unsuccessful in finding NOE correlations to assign its stereochemistry. The spirocentre stereochemistry is therefore not known in this case.
  • 41
    • 0021947264 scopus 로고
    • For α,β-unsaturated aldehyde reduction, see
    • (a) For α,β-unsaturated aldehyde reduction, see: Stevens, R. V.; Lawrence, D. S. Tetrahedron 1985, 41, 93.
    • (1985) Tetrahedron , vol.41 , pp. 93
    • Stevens, R.V.1    Lawrence, D.S.2
  • 42
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    • For Birch reduction, see ref 7j
    • (b) For Birch reduction, see ref 7j.
  • 43
    • 49949128203 scopus 로고
    • The original paper concerns the effect of conformation of a stereocentre a to a carbonyl group on facial selectivity of nucleophilic addition to the carbonyl
    • (a) The original paper concerns the effect of conformation of a stereocentre a to a carbonyl group on facial selectivity of nucleophilic addition to the carbonyl: Cherest, M.; Felkin, H.; Prudent, N. Tetrahedron Lett. 1968, 2199.
    • (1968) Tetrahedron Lett. , pp. 2199
    • Cherest, M.1    Felkin, H.2    Prudent, N.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.