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Volumn 12, Issue 14, 2014, Pages 2180-2184

Straightforward access to 4-membered sulfurated heterocycles: Introducing a strategy for the single and double functionalization of thietane 1-oxide

Author keywords

[No Author keywords available]

Indexed keywords

ELECTROPHILES; FUNCTIONALIZATIONS; FUNCTIONALIZED; HETEROCYCLES; ORGANOMETALLIC INTERMEDIATES; STEREO-SELECTIVE; THIETANES;

EID: 84903369181     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/c4ob00173g     Document Type: Article
Times cited : (21)

References (41)
  • 1
    • 84865443841 scopus 로고    scopus 로고
    • Four-Membered Heterocycles: Structure and Reactivity
    • in, ed. J. Alvarez-Builla, J. J. Vaquero and J. Barluenga, Wiley-VCH, ch. 3, 163-268
    • G. Rousseau and S. Robin, Four-Membered Heterocycles: Structure and Reactivity, in Modern Heterocyclic Chemistry, ed., J. Alvarez-Builla, J. J. Vaquero, and, J. Barluenga, Wiley-VCH, ch. 3, 2011, pp. 163-268
    • (2011) Modern Heterocyclic Chemistry
    • Rousseau, G.1    Robin, S.2
  • 19
    • 77955732976 scopus 로고    scopus 로고
    • WO 2008035315 A2 20080327, For a recent work on the importance in drug-discovery of small-sized saturated heterocycles see
    • S. Rudra et al. PCT Int. Appl, WO 2008035315 A2 20080327, 2008
    • (2008) PCT Int. Appl
    • Rudra, S.1
  • 36
    • 6444228185 scopus 로고
    • We use the trans/cis descriptors with reference to the spatial relationship between the introduced electrophile and the oxygen atom of the SO group CCDC number of cis- 2a. The crystallographic analysis of the cis- 2a, revealed a puckered conformation for the four-membered ring, an equatorial benzhydryl group and an intramolecular hydrogen bond between the hydroxyl group and the axial oxygen atom of the sulfinyl group (see ESI) Stereochemical issues have been reported in the lithiation/functionalization of thiane oxide, see
    • J. F. King J. R. Du Manoir Can. J. Chem. 1973 51 4082
    • (1973) Can. J. Chem. , vol.51 , pp. 4082
    • King, J.F.1    Du Manoir, J.R.2
  • 38
    • 0000232886 scopus 로고
    • To shed light on this intriguing process, spectroscopic and computational investigations are underway to prove the configurational (in)stability and the structure in solution of 1-Li and the stereochemical course of its reaction with electrophile (retentive or invertive). A planar intermediate could not be ruled out as demonstrated for the closely related thiane 1-oxide, see
    • G. Chassaing R. Lett A. Marquet Tetrahedron Lett. 1978 19 471
    • (1978) Tetrahedron Lett. , vol.19 , pp. 471
    • Chassaing, G.1    Lett, R.2    Marquet, A.3
  • 39
    • 0004446358 scopus 로고
    • ref. 18b The trans/cis descriptors are used to indicate the relative configuration of the functionalized carbons C2 and C4 A double functionalization has been reported in the lithiation of thiane-1-oxide derivatives see
    • R. Lett G. Chassaig Tetrahedron 1978 34 2705
    • (1978) Tetrahedron , vol.34 , pp. 2705
    • Lett, R.1    Chassaig, G.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.