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Volumn 63, Issue 12, 1998, Pages 4120-4124

Asymmetric Allylation and Reduction on an Ephedrine-Derived Template: Stereoselective Synthesis of α-Hydroxy Acids and Derivatives

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EID: 0000862469     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9722820     Document Type: Article
Times cited : (44)

References (43)
  • 9
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    • and references therein. Ene reactions of pyruvates
    • Asymmetric ene reactions of glyoxylates: a) Whitesell, J. K.; Bhattacharya, A.; Buchanan, C. M.; Chen, H. H.; Deyo, D.; James, D.; Liu, C.-L.; Minton, M. A. Tetrahedron 1986, 42, 2993-3001. (b) Mikami, K. Pure Appl. Chem. 1996, 68, 639 and references therein. Ene reactions of pyruvates:
    • (1996) Pure Appl. Chem. , vol.68 , pp. 639
    • Mikami, K.1
  • 19
    • 0029089534 scopus 로고
    • For a stereodivergent reduction of prolinol based hemiacetals of α-keto acids see: Pansare, S. V.; Ravi, R. G. Tetrahedron Lett. 1995, 36, 5959-5962.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 5959-5962
    • Pansare, S.V.1    Ravi, R.G.2
  • 20
    • 85034486756 scopus 로고    scopus 로고
    • note
    • Hemiacetal 1d: colorless, orthorhombic crystals; space group P212121; unit cell parameters, a = 8.083(2) Å, b = 9.135(4) Å, c = 40.635(5) Å; α = 90°, β= 90°, γ = 90°; Z = 8, R (I > 2σ(I)) = 0.0495, GOF = 1.119. Hemiacetal 1e: colorless, orthorhombic crystals; space group P212121- unit cell parameters, a = 8.256(5) Å, b = 9.522(2) Å, c = 18.836(4) Å; α = 90°, β= 90°, γ = 90°; Z = 4, R (I > 2σ(I)) = 0.0365, GOF = 1.071.
  • 24
    • 85034483898 scopus 로고    scopus 로고
    • note
    • 13C NMR.
  • 25
    • 0000943833 scopus 로고
    • The stereochemical assignment is based on the reported trend in chemical shifts for the olefinic methine protons in (E) and (Z)-benzylidenecamphor derivatives, see: Kossanyi, J.; Furth, B.; Morizur, J. P. Tetrahedron 1970, 26, 395-409.
    • (1970) Tetrahedron , vol.26 , pp. 395-409
    • Kossanyi, J.1    Furth, B.2    Morizur, J.P.3
  • 26
    • 0000087168 scopus 로고
    • The alkylation of an ephedrine-based glycolic acid derivative has been briefly described. However, removal of the ephedrine portion was not investigated due to potential difficulties; see: Ludwig, J. W.; Newcomb, M.; Bergbreiter, D. E. Tetrahedron Lett. 1986, 27, 2731-2734.
    • (1986) Tetrahedron Lett. , vol.27 , pp. 2731-2734
    • Ludwig, J.W.1    Newcomb, M.2    Bergbreiter, D.E.3
  • 27
    • 85034468001 scopus 로고    scopus 로고
    • note
    • Dissolving metal reduction of 2a generated a mixture of Products arising from cleavage of both the benzylic C-O bonds and other side reactions. Other methods for regioselective cleavage of 2a are being examined.
  • 32
    • 0000876573 scopus 로고
    • (a) Chiral glycine derivatives: Vigneron J. P.; Kagan, H.; Horeau, A. Tetrahedron Lett. 1968, 5681-5683. Sinclair, P. J.; Zhai, D.; Reibenspies, J.; Williams, R. M. J. Am. Chem. Soc. 1986, 108, 1103-1104. Williams, R. M. Aldrichim. Acta 1992, 25, 11-25.
    • (1968) Tetrahedron Lett. , pp. 5681-5683
    • Vigneron, J.P.1    Kagan, H.2    Horeau, A.3
  • 33
    • 0000599790 scopus 로고
    • (a) Chiral glycine derivatives: Vigneron J. P.; Kagan, H.; Horeau, A. Tetrahedron Lett. 1968, 5681-5683. Sinclair, P. J.; Zhai, D.; Reibenspies, J.; Williams, R. M. J. Am. Chem. Soc. 1986, 108, 1103-1104. Williams, R. M. Aldrichim. Acta 1992, 25, 11-25.
    • (1986) J. Am. Chem. Soc. , vol.108 , pp. 1103-1104
    • Sinclair, P.J.1    Zhai, D.2    Reibenspies, J.3    Williams, R.M.4
  • 34
    • 0001459021 scopus 로고
    • (a) Chiral glycine derivatives: Vigneron J. P.; Kagan, H.; Horeau, A. Tetrahedron Lett. 1968, 5681-5683. Sinclair, P. J.; Zhai, D.; Reibenspies, J.; Williams, R. M. J. Am. Chem. Soc. 1986, 108, 1103-1104. Williams, R. M. Aldrichim. Acta 1992, 25, 11-25.
    • (1992) Aldrichim. Acta , vol.25 , pp. 11-25
    • Williams, R.M.1
  • 36
    • 85034479305 scopus 로고    scopus 로고
    • note
    • Extended reaction times lead to the exclusive formation of a dimeric product that probably arises from reaction of the enol ether in 3b with the oxocarbenium ion derived from 1b.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.