Studies on the diastereoselectivity of samarium(II) iodide mediated reductive carbocyclizations of ω-iodo-α,β-unsaturated esters prepared from 2-deoxy-D-ribose

Tetrahedron Letters

Volumn 39, Issue 39, 1998, Pages 7075-7078

  Bennett, Sharon M ^a   Biboutou, Raphinos Kouya ^a   Salari, Bita Samim Firouz ^a  

^a UNIVERSITÉ DU QUÉBEC À MONTRÉAL   (Canada)

Author keywords

Alkenyl halides; Carbohydrates; Cyclisation; Samarium and compounds

Indexed keywords

2 DEOXYRIBOSE; ALKENYL GROUP; CARBOHYDRATE; ESTER; HALIDE; REAGENT; SAMARIUM;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; DIASTEREOISOMER; GEOMETRY; STEREOCHEMISTRY;

EID: 0032563821     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01552-4     Document Type: Article

References (26)

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16. 3SnH mediated radical cyclizations of ω-bromo-α,β-unsaturated ethyl esters, derived from D-ribonolactone, have been reported in the literature. See: Wilcox, C.S.; Thomasco, L.M. J. Org. Chem. 1985, 50, 546-547.
17. 8. For a discussion on the stereochemistry of radical cyclizations see: Curran, D.P.; Porter, N.A.; Giese, B. Stereochemistry of Radical Reactions - Concepts, Guidelines and Synthetic Applications, VCH, Weinheim, 1996.
18. 4a (equation presented)
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24. 3SnH (1.4 eq) and AIBN (0.1 eq) was prepared at rt under anhyd conditions under an argon atmosphere and then heated to 80 °C. The workup was as described in reference 4a.
25. 2 mediated intermolecular coupling of α-(alkoxycarbonyl)amino ketones with α,β-unsaturated esters. See: Kawatsura, M.; Dekura, F.; Shirahama, H.; Matsuda, F. Synlett 1996, 373-376.
26. 9