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Volumn 64, Issue 5, 1999, Pages 1727-1732

A short and efficient route to enantiopure 3,5-diarylpyrrolizidines

Author keywords

[No Author keywords available]

Indexed keywords

HETEROCYCLIC AMINE; PYRROLIZIDINE DERIVATIVE;

EID: 0033525850     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981946i     Document Type: Note
Times cited : (9)

References (32)
  • 16
    • 0039967449 scopus 로고
    • Cis-fused pyrrolizidines are normally more stable than the corresponding trans-fused compounds (see ref 13a). 3,5-Dimethylpyrrolizidines having the cis relative configuration for the two methyl groups are instead reported to have a trans-fused stereochemistry for the ring junction. Antipova, I. V.; Negrebetskii, V. V.; Skvortsov, I. M. Khim. Geterotsikl. Soed. 1982, 39-46.
    • (1982) Khim. Geterotsikl. Soed. , pp. 39-46
    • Antipova, I.V.1    Negrebetskii, V.V.2    Skvortsov, I.M.3
  • 17
    • 0344869615 scopus 로고    scopus 로고
    • note
    • We also tried to generate the 4-amino group by hydrogenation (over Raney Nickel in MeOH) of the 4-nitro-1,7-dimesylate derivatives obtained by reaction of 3a,b with MsCl in dichloromethane (route not shown in Scheme 1). However, this procedure was ineffective in yielding cyclization products, since solvolysis of the O-mesyl groups (to give mixtures of 1,7-dimethoxy-substituted products) was much faster than the reduction of the nitro to amino group.
  • 23
    • 0001694460 scopus 로고
    • In cyclic systems, the protons adjacent to the nitrogen atom and on the same side of the N lone pair undergo a strong deshielding effect, whereas the protons on the opposite side are strongly shielded: (a) Crabb, T. A.; Newton, R. F.; Jackson, D. Chem. Rev. 1971, 71, 109-126.
    • (1971) Chem. Rev. , vol.71 , pp. 109-126
    • Crabb, T.A.1    Newton, R.F.2    Jackson, D.3
  • 27
    • 0344869612 scopus 로고
    • Manske, R. H. F., Ed.; Academic Press: New York, Chapter 5
    • (e) Bohlmann, F.; Shumann, D. In The Alkaloids; Manske, R. H. F., Ed.; Academic Press: New York, 1967; Vol IX, Chapter 5.
    • (1967) The Alkaloids , vol.9
    • Bohlmann, F.1    Shumann, D.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.