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Volumn 71, Issue 14, 2006, Pages 5198-5207

Synthesis of 2,4-disubstituted piperidines via radical cyclization: Unexpected enhancement in diastereoselectivity with tris(trimethylsilyl)silane

Author keywords

[No Author keywords available]

Indexed keywords

2, 4, DISUBSTITUTED PIPERIDINES; STEREOISOMER; TRIBUTYLTIN HYDRIDE; TRIS(TRIMETHYLSILYL)SILANE;

EID: 33745700322     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060495w     Document Type: Article
Times cited : (43)

References (84)
  • 1
    • 77957051048 scopus 로고
    • Brossi, A., Ed.; Academic Press: London
    • (a) Findlay, J. A. In The Alkaloids: Brossi, A., Ed.; Academic Press: London, 1985; Vol. 26, pp 89-183.
    • (1985) The Alkaloids , vol.26 , pp. 89-183
    • Findlay, J.A.1
  • 10
    • 0034676585 scopus 로고    scopus 로고
    • Between July 1988 and December 1998 over 12 000 piperidines were mentioned in clinical and preclinical studies. See: Watson, P. S.; Jiang, B.; Scott, B. Org. Lett. 2000, 2, 3679-3681.
    • (2000) Org. Lett. , vol.2 , pp. 3679-3681
    • Watson, P.S.1    Jiang, B.2    Scott, B.3
  • 48
  • 65
    • 33748542524 scopus 로고
    • 1,3 strain in piperidines is reviewed in: Johnson, F. Chem. Rev. 1968, 68, 375-413.
    • (1968) Chem. Rev. , vol.68 , pp. 375-413
    • Johnson, F.1
  • 66
    • 33845470921 scopus 로고
    • For examples of the phenomenon in N-acyl, N-sulfonyl and related piperidines see: (a) Beak, P.; Zajdel, W. J. J. Am. Chem. Soc. 1984, 106, 1010-1018.
    • (1984) J. Am. Chem. Soc. , vol.106 , pp. 1010-1018
    • Beak, P.1    Zajdel, W.J.2
  • 81
    • 0036679560 scopus 로고    scopus 로고
    • Work by Studer and Zard suggests that sulfur dioxide extrusion from aminosulfonyl radicals is a slow process, so another possibility is that 21 undergoes C-S bond cleavage to give an aminosulfonyl radical which is trapped by TTMSS before undergoing sulfur dioxide extrusion to afford 23. See ref 24 and also: Bossart, M.; Fassler, R.; Schoenberger, J.; Studer, A. Eur. J. Org. Chem. 2002, 2742-2757.
    • (2002) Eur. J. Org. Chem. , pp. 2742-2757
    • Bossart, M.1    Fassler, R.2    Schoenberger, J.3    Studer, A.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.