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Volumn 2, Issue 7, 1996, Pages 894-900

Diastereoselective zwitterionic aza-Claisen rearrangement: Synthesis of nine-membered ring lactams and transannular ring contraction

Author keywords

Aza Claisen rearrangement; Azoninones; Indolizidinones; Ring contractions

Indexed keywords

ASYMMETRIC INDUCTION; AZA-CLAISEN REARRANGEMENT; AZONINONES; DIASTEREO-SELECTIVITY; INDOLIZIDINONES; NINE-MEMBERED RINGS; RING CONTRACTION; SUBSTITUTION PATTERNS;

EID: 0000805388     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.19960020721     Document Type: Article
Times cited : (29)

References (39)
  • 17
    • 0000710639 scopus 로고
    • N-Benzylproline methyl ester 3
    • N-Benzylproline methyl ester 3: E. J. Corey, J. O. Link, J. Org. Chem. 1991, 56, 442.
    • (1991) J. Org. Chem. , vol.56 , pp. 442
    • Corey, E.J.1    Link, J.O.2
  • 25
    • 84891306399 scopus 로고    scopus 로고
    • note
    • The reaction was not complete after 3 weeks; about 50% of aminoester 4 was recycled. Only small amounts of allylchlorides 10 and 11 were formed. The second diastereoisomer could not be obtained in pure form (mixture with the von Braun type products).
  • 26
    • 84891304884 scopus 로고    scopus 로고
    • note
    • Similar results were achieved by replacing the terminal benzyloxy group by a hydrogen. Chloroacetyl chloride only generated the corresponding azoninone in poor yields (about 10%) and a disappointing diastereoselectivity (anti:syn = 1.2:1). Most of the allylamine employed generated the von Braun type products 10 and 11.
  • 37
    • 0001377606 scopus 로고
    • Methoden Org. Chem. (Houben - Weyl). Thieme, Stuttgart, New York
    • a) H. Frauenrath in Methoden Org. Chem. (Houben - Weyl). Vol. E21d: Stereoselective Synthesis, Thieme, Stuttgart, New York, 1995, 3301.
    • (1995) Stereoselective Synthesis , vol.E21D , pp. 3301
    • Frauenrath, H.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.