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Volumn , Issue 24, 2002, Pages 4190-4194

Diastereoselective synthesis of α-methylpyroglutamates from α,β-didehydro α-amino acids

Author keywords

Amino acids; Diastereoselectivity; Lactams; Lithiation; Ring contraction

Indexed keywords

2 BENZYL 6 (1 HYDROXY 1 METHYLETHYL) 4,5 DIHYDROPYRIDAZIN 3(2H) ONE; 2 BENZYL 6 (1 HYDROXY 1 METHYLETHYL) 4,5 DIMETHYL 4,5 DIHYDROPYRIDAZIN 3(2H) ONE; 2 BENZYL 6 (1 HYDROXY 1 METHYLETHYL) 5 METHYL 4,5 DIHYDROPYRIDAZIN 3(2H) ONE; 2 BENZYL 6 (1 HYDROXY 1 METHYLETHYL) 5 PHENYL 4,5 DIHYDROPYRIDAZIN 3(2H) ONE; AMINO ACID DERIVATIVE; GLUTAMIC ACID DERIVATIVE; PYRIDAZINE DERIVATIVE; PYRROLIDINE DERIVATIVE; TERT BUTYL 1 BENZYL 3 METHYL 4 PHENYL 6 OXOPERHYDROPYRIDAZINE 3 CARBOXYLATE; TERT BUTYL 1 BENZYL 3 METHYL 6 OXOPERHYDROPYRIDAZINE 3 CARBOXYLATE; TERT BUTYL 1 BENZYL 3,4 DIMETHYL 6 OXOPERHYDROPYRIDAZINE 3 CARBOXYLATE; TERT BUTYL 1 BENZYL 3,4,5 TRIMETHYL 6 OXOPERHYDROPYRIDAZINE 3 CARBOXYLATE; TERT BUTYL 1 BENZYLAMINO 2 METHYL 5 OXOPYRROLIDINE 2 CARBOXYLATE; TERT BUTYL 1 BENZYLIDENAMINO 2 METHYL 5 OXO 3 PHENYLPYRROLIDINE 2 CARBOXYLATE; TERT BUTYL 1 BENZYLIDENAMINO 2 METHYL 5 OXOPYRROLIDINE 2 CARBOXYLATE; TERT BUTYL 1 BENZYLIDENAMINO 2,3 DIMETHYL 5 OXOPYRROLIDINE 2 CARBOXYLATE; TERT BUTYL 1 BENZYLIDENAMINO 2,3,4 TRIMETHYL 5 OXOPYRROLIDINE 2 CARBOXYLATE; TERT BUTYL 2 METHYL 5 OXO 3 PHENYLPYRROLIDINE 2 CARBOXYLATE; TERT BUTYL 2 METHYL 5 OXOPYRROLIDINE 2 CARBOXYLATE; TERT BUTYL 2,3 DIMETHYL 5 OXOPYRROLIDINE 2 CARBOXYLATE; TERT BUTYL 2,3,4 TRIMETHYL 5 OXOPYRROLIDINE 2 CARBOXYLATE; UNCLASSIFIED DRUG;

EID: 0036910377     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200212)2002:24<4190::AID-EJOC4190>3.0.CO;2-Q     Document Type: Article
Times cited : (6)

References (32)
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    • The creation of asymmetric quaternary centres is one of the most challenging problems in organic chemistry. See, for example: [8a] K. Fuji, Chem. Rev. 1993, 93, 2037. [8b] E. J. Corey, A. Guzman Pérez, Angew. Chem. Int. Ed. 1998, 37, 388. [8c] J. Christoffers, A. Mann, Angew. Chem. Int. Ed. 2001, 40, 4591.
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    • For other diastereoselective syntheses of pyroglutamates starting from glycine imines see: [11a] C. Alvarez Ibarra, A. G. Csákÿ, M. Maroto, M. L. Quiroga, J. Org. Chem. 1995, 60, 6700. [11b] C. Alvarez Ibarra, A. G. Csákÿ I. López de Silanes, M. L. Quiroga, J. Org. Chem. 1997, 62, 479 and references cited therein.
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    • and references cited therein
    • For other diastereoselective syntheses of pyroglutamates starting from glycine imines see: [11a] C. Alvarez Ibarra, A. G. Csákÿ, M. Maroto, M. L. Quiroga, J. Org. Chem. 1995, 60, 6700. [11b] C. Alvarez Ibarra, A. G. Csákÿ I. López de Silanes, M. L. Quiroga, J. Org. Chem. 1997, 62, 479 and references cited therein.
    • (1997) J. Org. Chem. , vol.62 , pp. 479
    • Alvarez Ibarra, C.1    Csákÿ, A.G.2    López de Silanes, I.3    Quiroga, M.L.4
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    • note
    • This stereochemistry is in agreement with that previously observed for the reduction of compounds 2, 3. See ref.[10]
  • 31
    • 0012169493 scopus 로고    scopus 로고
    • note
    • Epimerization of the final products 9 may also account for the same result.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.