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Volumn 43, Issue 26, 2004, Pages 3445-3448

Dithiocarbamate group transfer cyclization reactions of carbamoyl radicals under "tin-free" conditions

Author keywords

Cyclization; Group transfer; Lactams; Radical reactions; Synthetic methods

Indexed keywords

HEATING; INITIATORS (CHEMICAL); NITROGEN; REACTION KINETICS;

EID: 4544326488     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200453600     Document Type: Article
Times cited : (53)

References (61)
  • 4
    • 0004269715 scopus 로고    scopus 로고
    • (Eds.: P. Renaud, M. P. Sibi), Wiley-VCH, Weinheim
    • d) Radicals in Organic Synthesis, Vol. 1-2 (Eds.: P. Renaud, M. P. Sibi), Wiley-VCH, Weinheim, 2001.
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  • 6
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    • a) P. A. Baguley, J. C. Walton, Angew. Chem. 1998, 110, 3272; Angew. Chem. Int. Ed. 1998, 37, 3072;
    • (1998) Angew. Chem. Int. Ed. , vol.37 , pp. 3072
  • 8
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    • S. Z. Zard, Angew. Chem. 1997, 109, 724; Angew. Chem. Int. Ed. Engl. 1997, 36, 672, and references therein.
    • (1997) Angew. Chem. , vol.109 , pp. 724
    • Zard, S.Z.1
  • 9
    • 0030802574 scopus 로고    scopus 로고
    • and references therein
    • S. Z. Zard, Angew. Chem. 1997, 109, 724; Angew. Chem. Int. Ed. Engl. 1997, 36, 672, and references therein.
    • (1997) Angew. Chem. Int. Ed. Engl. , vol.36 , pp. 672
  • 22
    • 0003168906 scopus 로고    scopus 로고
    • for reviews on nitrogen-centered radicals see: c) S. Z. Zard, Synlett 1996, 1148;
    • (1996) Synlett , pp. 1148
    • Zard, S.Z.1
  • 25
    • 0032482096 scopus 로고    scopus 로고
    • a) L. Boiteau, J. Boivin, A. Liard, B. Quiclet-Sire, S. Z. Zard, Angew. Chem. 1998, 110, 1197; Angew. Chem. Int. Ed. 1998, 37, 1128;
    • (1998) Angew. Chem. Int. Ed. , vol.37 , pp. 1128
  • 45
    • 0037433267 scopus 로고    scopus 로고
    • Additions of tin radicals and a range of other carbon-centered radicals to thiocarbonyl groups are regarded as fast compared to other competitive processes; see for example refs. [3,5]. For alternative reaction modes of xanthates and thiourethanes in the Barton-McCombie reaction, see: J. U. Rhee, B. I. Bliss, T. V. RajanBabu, J. Am. Chem. Soc. 2003, 125, 1492.
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 1492
    • Rhee, J.U.1    Bliss, B.I.2    RajanBabu, T.V.3
  • 48
    • 4544232230 scopus 로고    scopus 로고
    • note
    • The formation of products analogous to 8 and 9 has been observed by Zard in his preparation of acyl radical precursors. In his case careful control of the stoichiometry (xanthate salt):(acid chloride) together with the correct order of addition was sufficient to ensure good yields of the radical precursor. See ref. [3].
  • 49
    • 4544325684 scopus 로고    scopus 로고
    • note
    • The incorporation of a Cbz group in place of the benzyl group could not be achieved. Keck has reported an example of a carbamoyl xanthate where the nitrogen atom is part of an oxazolidinone ring; see ref. [9h].
  • 50
    • 4544283811 scopus 로고    scopus 로고
    • (DuPont de Nemours), US 2171420, 1939
    • I. Williams (DuPont de Nemours), US 2171420, 1939.
    • Williams, I.1
  • 51
    • 4544284519 scopus 로고    scopus 로고
    • note
    • All dithiocarbamate radical precursors were prepared in > 80% yield from the corresponding secondary amine in a two-step procedure (see Experimental Section), with the exception of 14 which was prepared from the corresponding tertiary dimethylamine.
  • 52
    • 4544236795 scopus 로고    scopus 로고
    • note
    • The coupling constants for the proton on the carbon atom adjacent to the sulfur atom in both 15 and 16 are consistent with an equatorial arrangement of the dithiocarbamate group on the cyclohexane ring. This proton shows a NOE interaction to one of the pyrrolidinone ring hydrogen atoms in the case of 15, whereas no NOE interaction is observed to either of these hydrogen atoms in the case of 16. (diagram presented)
  • 55
    • 0033618523 scopus 로고    scopus 로고
    • for a review on free-radical methods for the synthesis of medium-size rings, see: c) L. Yet, Tetrahedron 1999, 55, 9349.
    • (1999) Tetrahedron , vol.55 , pp. 9349
    • Yet, L.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.