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Volumn 107, Issue 1, 1985, Pages 273-274

Enantioselective Synthesis of Quaternary Carbon Centers through Michael-Type Alkylation of Chiral Imines

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EID: 0000257169 PISSN: 00027863 EISSN: 15205126 Source Type: Journal
DOI: 10.1021/ja00287a061 Document Type: Letter

Times cited : (234)

References (7)

1
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- Port-Camargue, France, April
- Pfau, M.; Revial, G.; Guingant, A.; d'Angelo, J., paper presented in part at the EUCHEM Conference on Asymmetric Formation of C-C Bonds, Port-Camargue, France, April 25–27, 1984.
- (1984) paper presented in part at the EUCHEM Conference on Asymmetric Formation of C-C Bonds , pp. 25-27
- Pfau, M.¹ Revial, G.² Guingant, A.³ d'Angelo, J.⁴

2
- 0000449913
- For an excellent review on the construction of quaternary carbon centers, see
- For an excellent review on the construction of quaternary carbon centers, see: Martin, S. F. Tetrahedron 1980, 36, 419–460.
- (1980) Tetrahedron , vol.36 , pp. 419-460
- Martin, S.F.¹

3
- 0009653666
- 2 carbon centers: Kogen, H.; Tomioka, K.; Hashimoto, S.; Koga, K. Tetrahedron 1981, 37, 3951–3956. Posner, G. H.; Kogan, T. P.; Hulce, M. Tetrahedron Lett. 1984, 383–386. Enantiotopic group differentiation from prochiral precursors bearing quaternary carbon centers (chemical or enzymatic methods): Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39, 1615–1621. Brooks, D. W.; Grothaus, P. G.; Irwin, W. L. J. Org. Chem. 1982, 47, 2820–2821. Schneider, M.; Engel, N.; Boensmann, H. Angew. Chem., Int. Ed. Engl. 1984, 23, 66
- 2 carbon centers: Kogen, H.; Tomioka, K.; Hashimoto, S.; Koga, K. Tetrahedron 1981, 37, 3951–3956. Posner, G. H.; Kogan, T. P.; Hulce, M. Tetrahedron Lett. 1984, 383–386. Enantiotopic group differentiation from prochiral precursors bearing quaternary carbon centers (chemical or enzymatic methods): Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39, 1615–1621. Brooks, D. W.; Grothaus, P. G.; Irwin, W. L. J. Org. Chem. 1982, 47, 2820–2821. Schneider, M.; Engel, N.; Boensmann, H. Angew. Chem., Int. Ed. Engl. 1984, 23, 66.
- (1969) Tetrahedron Lett. , pp. 4237-4240
- Yamada, S.¹ Otani, G.²

4
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- (b) Pfau, M.; Ribiére, C. Bull. Soc. Chim. Fr. 1971, 2584–2590 (c) Pfau, M.; Ribiére, C. Bull. Soc. Chim. Fr. 1976, 776–780. (d) Pfau, M.; Ughetto-Monfrin, J. Tetrahedron 1979, 35, 1899–1904. (e) Pfau, M.; Ughetto-Monfrin, J.; Joulain, D. Bull. Soc. Chim. Fr. 1979, 627–632
- Pfau, M.; Ribiére, C. J. Chem. Soc., Chem. Commun. 1970, 66–67. (b) Pfau, M.; Ribiére, C. Bull. Soc. Chim. Fr. 1971, 2584–2590. (c) Pfau, M.; Ribiére, C. Bull. Soc. Chim. Fr. 1976, 776–780. (d) Pfau, M.; Ughetto-Monfrin, J. Tetrahedron 1979, 35, 1899–1904. (e) Pfau, M.; Ughetto-Monfrin, J.; Joulain, D. Bull. Soc. Chim. Fr. 1979, 627–632.
- (1970) Chem. Soc., Chem. Commun. , pp. 66-67
- Pfau, M.¹ Ribiére, C.J.²

5
- 0039497736
- As previously reported, the alkylation takes place exclusively at the more substituted carbon atom, see ref 6d and p 3411 of
- As previously reported, the alkylation takes place exclusively at the more substituted carbon atom, see ref 6d and p 3411 of: Hickmott, P. W. Tetrahedron 1982, 38, 3363–3446.
- (1982) Tetrahedron , vol.38 , pp. 3363-3446
- Hickmott, P.W.¹

6
- 0001570711
- 24D-207° (c 1, EtOH)
- C.R., Johnson, J.R., Zeller, J. Am. Chem. Soc., Following specific rotation was reported for pure (R)-(-)-octalone 11: [α], 24, D-207° (c 1, EtOH), (1982), 104, 4021-4023
- (1982) J. Am. Chem. Soc. , vol.104 , pp. 4021-4023
- Johnson, C.R.¹ Zeller, J.R.²

7
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- Weill-Raynal, J. Synthesis 1969, 49-56.
- (1969) Synthesis , pp. 49-56
- Weill-Raynal, J.¹

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