메뉴 건너뛰기




Volumn 69, Issue 11, 2004, Pages 3976-3978

Endo-selective quenching of hexahydropyrrolo[2,3-b]indole-based N-acyliminium ions

Author keywords

[No Author keywords available]

Indexed keywords

CRYSTALLOGRAPHY; NUCLEAR MAGNETIC RESONANCE; QUENCHING; SILANES; STEREOCHEMISTRY;

EID: 2442651496     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049757p     Document Type: Article
Times cited : (8)

References (36)
  • 23
    • 0011167360 scopus 로고
    • Brossi, A., Ed.; Academic Press: New York
    • Hino, T.; Nakagawa, M. In Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1988; Vol. 34, pp 1-75.
    • (1988) Alkaloids , vol.34 , pp. 1-75
    • Hino, T.1    Nakagawa, M.2
  • 30
    • 2442637109 scopus 로고    scopus 로고
    • note
    • The absolute configuration for chiral C-atoms was unambiguously determined as 2R,3aS,8aS and the carbamate partial double bond is reflected in the short distance N1-C9, 1.369(4) Å.
  • 31
    • 85087606111 scopus 로고    scopus 로고
    • note
    • 2Ph moiety along the N8-S1 bond. On the other hand, the formation of a double bond during the ring opening is confirmed by bond lengths C3a-C8a = 1.333(6) and 1.345(6) Å for the first and second molecule, respectively.
  • 32
    • 2442655974 scopus 로고    scopus 로고
    • note
    • The cyano group is characterized by a formal triple bond, C13-N14 = 1. 127 (5) Å; the configuration for C3a and C8a remains unchanged relative to starting material, while the C2 atom presents now an S configuration.
  • 34
    • 2442647143 scopus 로고    scopus 로고
    • note
    • 36 pyrrolidine derived iminium ions, neighboring group participation from the carbamoyl or sulfonyl group has been invoked as a possible explanation for the stereoselectivity. While this may be possible with the N-sufonyl system, with the tetrahedral sulfur and longer N-S and S-O bonds, it seems unlikely in N-carbamoyl systems, such as those described here, when it would require the disruption of the crystallographically well-established N=C(O-)OMe double bond character.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.