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Volumn 2, Issue 15, 2000, Pages 2185-2187

Diastereoselective protonation of lactam enolates derived from (R)-phenylglycinol. A novel asymmetric route to 4-phenyl-1,2,3,4-tetrahydroisoquinolines

Author keywords

[No Author keywords available]

Indexed keywords

(4S) N METHYL 4 PHENYL 1,2,3,4 TETRAHYDROISOQUINOLINE; (4S)-N-METHYL-4-PHENYL-1,2,3,4-TETRAHYDROISOQUINOLINE; 1,2,3,4 TETRAHYDRO 4 PHENYLISOQUINOLINE; 4-PHENYL-1,2,3,4-TETRAHYDROISOQUINOLINE; DRUG DERIVATIVE; GLYCINE; ISOQUINOLINE DERIVATIVE; LACTAM; NEUROTRANSMITTER UPTAKE INHIBITOR; PHENYLGLYCINOL; PROTON; TETRAHYDROISOQUINOLINE DERIVATIVE;

EID: 0034720942     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0057939     Document Type: Article
Times cited : (31)

References (25)
  • 1
    • 0001251131 scopus 로고
    • For a review on asymmetric synthesis of 1-substituted tetrahydroisoquinolines, see: Rozwadowska, M. D. Heterocycles 1994, 39, 903.
    • (1994) Heterocycles , vol.39 , pp. 903
    • Rozwadowska, M.D.1
  • 11
    • 0032572893 scopus 로고    scopus 로고
    • (b) This approach, based on Husson's methodology first developed in the piperazine series, has been applied afterwards in the tetrahydroisoquinoline series as well. Roussi, F.; Quirion, J. C.; Tomas, A.; Husson, H. P. Tetrahedron 1998, 54, 10363.
    • (1998) Tetrahedron , vol.54 , pp. 10363
    • Roussi, F.1    Quirion, J.C.2    Tomas, A.3    Husson, H.P.4
  • 12
    • 0021127516 scopus 로고
    • For phenylation of enolates with diphenyliodonium salts, see: (a) Varvoglis, A. Synthesis 1984, 709.
    • (1984) Synthesis , pp. 709
    • Varvoglis, A.1
  • 16
    • 0032555634 scopus 로고    scopus 로고
    • This comparison has been done by Davies and Seebach in the course of studies related to diastereoselective alkylation and protonation of lithium enolates derived from chiral imidazolidinones or diketopiperazines. In both examples, whether alkyl halides or various proton sources are used to quench the corresponding enolates, the same diastereofacial selectivity is observed, see: Bull, S. D.; Davies, S. G.; Epstein, S. W.; Ouzman, J. V. A. Tetrahedron: Asymmetry 1998, 9, 2795. Seebach, D.; Dziadulewicz, E.; Behrendt, L.; Cantoreggi, S.; Fitzi, R. Liebigs Ann. Chem. 1989, 1215.
    • (1998) Tetrahedron: Asymmetry , vol.9 , pp. 2795
    • Bull, S.D.1    Davies, S.G.2    Epstein, S.W.3    Ouzman, J.V.A.4
  • 17
    • 84986674631 scopus 로고
    • This comparison has been done by Davies and Seebach in the course of studies related to diastereoselective alkylation and protonation of lithium enolates derived from chiral imidazolidinones or diketopiperazines. In both examples, whether alkyl halides or various proton sources are used to quench the corresponding enolates, the same diastereofacial selectivity is observed, see: Bull, S. D.; Davies, S. G.; Epstein, S. W.; Ouzman, J. V. A. Tetrahedron: Asymmetry 1998, 9, 2795. Seebach, D.; Dziadulewicz, E.; Behrendt, L.; Cantoreggi, S.; Fitzi, R. Liebigs Ann. Chem. 1989, 1215.
    • (1989) Liebigs Ann. Chem. , pp. 1215
    • Seebach, D.1    Dziadulewicz, E.2    Behrendt, L.3    Cantoreggi, S.4    Fitzi, R.5
  • 19
    • 0001161387 scopus 로고
    • (a) Our results, therefore, find analogy in the work of Askin. Indeed, alkylation of prolinol amide enolates with alkyl halides and epoxides takes place with opposite diastereoselectivity. This finding is interpreted by the author by an intermolecular chelation of the epoxide with the lithium alkoxide, see: Askin, D.; Volante, R. P.; Ryan, K. M. Tetrahedron lett. 1988, 29, 4245.
    • (1988) Tetrahedron Lett. , vol.29 , pp. 4245
    • Askin, D.1    Volante, R.P.2    Ryan, K.M.3
  • 20
    • 0030010210 scopus 로고    scopus 로고
    • (b) The same phenomenon has been observed with pseudoephedrine amide enolates. Myers, A. G.; McKinstry, L. J. Org. Chem. 1996, 61, 2428.
    • (1996) J. Org. Chem. , vol.61 , pp. 2428
    • Myers, A.G.1    McKinstry, L.2
  • 23
    • 0000654428 scopus 로고    scopus 로고
    • See ref 14b
    • For further preparation of 4-phenyl isochroman-3-one, see: Azzena, U.; Demartis, S.; Melloni, G. J. Org. Chem. 1996, 61, 4913. See ref 14b.
    • (1996) J. Org. Chem. , vol.61 , pp. 4913
    • Azzena, U.1    Demartis, S.2    Melloni, G.3
  • 24


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.