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Volumn 11, Issue 15, 2000, Pages 3211-3220

Stereoselective synthesis of syn-α-methyl-β-hydroxy esters

Author keywords

[No Author keywords available]

Indexed keywords

ESTER DERIVATIVE; KETONE DERIVATIVE; MACROLIDE;

EID: 0034637186     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(00)00274-3     Document Type: Article
Times cited : (10)

References (54)
  • 10
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    • Morrison, J. D., Ed.; Academic Press: New York
    • (c) Evans, D. A. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, pp. 1-110.
    • (1984) Asymmetric Synthesis , vol.3 , pp. 1-110
    • Evans, D.A.1
  • 20
    • 0000922736 scopus 로고    scopus 로고
    • Helmchen, G., Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart
    • (m) Braun, M. In Houben-Weyl's Methods of Organic Chemistry, Stereoselective Synthesis; Helmchen, G., Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1996; Vol. 3, pp. 1603-1666, 1713-1735.
    • (1996) Houben-Weyl's Methods of Organic Chemistry, Stereoselective Synthesis , vol.3 , pp. 1603-1666
    • Braun, M.1
  • 26
    • 0026327529 scopus 로고
    • The acetonide corresponding to (S)-1 can also be used in aldol reactions with good results (E. Falomir, PhD Thesis, University of Castellón, 1998). Ketone (S)-1, however, is obtained with a better yield from L-erythrulose. The acetonide corresponding to (R)-1 is known; see, for example: Ziegler, F. E.; Tung, J. S. J. Org. Chem. 1991, 56, 6530-6537.
    • (1991) J. Org. Chem. , vol.56 , pp. 6530-6537
    • Ziegler, F.E.1    Tung, J.S.2
  • 28
    • 0001222211 scopus 로고
    • (b) Mukaiyama, T.; Inoue, T. Bull. Chem. Soc. Jpn. 1980, 53, 174-178. For a general review on boron aldol additions, see: Cowden, C. J.; Paterson, I. Org. React. 1997, 51, 1-200.
    • (1980) Bull. Chem. Soc. Jpn. , vol.53 , pp. 174-178
    • Mukaiyama, T.1    Inoue, T.2
  • 29
    • 0001790298 scopus 로고    scopus 로고
    • (b) Mukaiyama, T.; Inoue, T. Bull. Chem. Soc. Jpn. 1980, 53, 174-178. For a general review on boron aldol additions, see: Cowden, C. J.; Paterson, I. Org. React. 1997, 51, 1-200.
    • (1997) Org. React. , vol.51 , pp. 1-200
    • Cowden, C.J.1    Paterson, I.2
  • 38
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    • (a) Cole, D. C. Tetrahedron 1994, 50, 9517-9582.
    • (1994) Tetrahedron , vol.50 , pp. 9517-9582
    • Cole, D.C.1
  • 47
    • 0028151214 scopus 로고
    • Paterson, I.; Wallace, D. J.; Velázquez, S. M. Tetrahedron Lett. 1994, 9083-9086. These authors suggested that initial formation of a five-membered chelate involving the boron, the carbonyl oxygen and the α oxygen atoms, followed by stereoselective deprotonation by the tertiary amine, explains the formation of a Z enolate. This and other alternative explanations are now being studied by us at both the theoretical and experimental level.
    • (1994) Tetrahedron Lett. , pp. 9083-9086
    • Paterson, I.1    Wallace, D.J.2    Velázquez, S.M.3
  • 48
  • 52
    • 0343055580 scopus 로고    scopus 로고
    • Computational ab initio calculations on enolization and aldolization processes are being performed by Dr. J. Murga and will be disclosed in due time
    • Computational ab initio calculations on enolization and aldolization processes are being performed by Dr. J. Murga and will be disclosed in due time.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.