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Volumn 38, Issue 46, 1997, Pages 8081-8084

Stereoselective radical C-C bond forming using Suarez' protocol: A non reductive process

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE DERIVATIVE; CYCLOPENTANE DERIVATIVE; RADICAL;

EID: 17144469329     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10114-9     Document Type: Article
Times cited : (13)

References (32)
  • 1
    • 0001562822 scopus 로고
    • For leading references see: (a)
    • For leading references see: (a) Hart, D.J. Science 1984, 223, 883.
    • (1984) Science , vol.223 , pp. 883
    • Hart, D.J.1
  • 19
    • 33748244854 scopus 로고
    • De Armas P., Francisco C.G., Suarez E.
    • de Armas, P.; Francisco, C.G.; Suarez, E. Angew. Chem., Int. Ed. Engl. 1992, 31, 772.
    • (1992) Angew. Chem., Int. Ed. Engl. , vol.31 , pp. 772
  • 22
    • 0342758817 scopus 로고    scopus 로고
    • In the case of entry 1 () the crude reaction mixture was chromatographed on silica gel, although the cyclic iodine was unstable on chromatography we obtained enough amounts to be identified
    • In the case of entry 1 ( ) the crude reaction mixture was chromatographed on silica gel, although the cyclic iodine was unstable on chromatography we obtained enough amounts to be identified.
  • 23
    • 0342323983 scopus 로고    scopus 로고
    • The following procedure is typical for the synthesis of 2: a solution of carbohydrate 1 (100 mg, 0.273 mmol) in dry benzene (8 ml) containing iodosylbenzene (180 mg, 0.819 mmol) and iodine (69 mg, 0.273 mmol) was desoxigenated by three cycles of freeze-pump-taw. The solution, under nitrogen, was refluxed for 3h. The reaction mixture was then poured into water and extracted with ether. The organic layer was washed with aqueous sodium thiosulfate and water. To the crude reaction mixture in benzene (3 ml) was added a spatula tip of AIBN and tri-Phenyltin hydride (0.084 ml, 0.33 mmol). This mixture was heated at reflux for 4h. Concentration and purification by flash chromatography (benzene/ethyl acetate 80:20 v/v) gave (40mg, 41%)
    • The following procedure is typical for the synthesis of 2: a solution of carbohydrate 1 (100 mg, 0.273 mmol) in dry benzene (8 ml) containing iodosylbenzene (180 mg, 0.819 mmol) and iodine (69 mg, 0.273 mmol) was desoxigenated by three cycles of freeze-pump-taw. The solution, under nitrogen, was refluxed for 3h. The reaction mixture was then poured into water and extracted with ether. The organic layer was washed with aqueous sodium thiosulfate and water. To the crude reaction mixture in benzene (3 ml) was added a spatula tip of AIBN and tri-Phenyltin hydride (0.084 ml, 0.33 mmol). This mixture was heated at reflux for 4h. Concentration and purification by flash chromatography (benzene/ethyl acetate 80:20 v/v) gave (40mg, 41%).
  • 32
    • 0342323981 scopus 로고    scopus 로고
    • For oxidation of stabilized tertiary radical involved iodine see: b
    • For oxidation of stabilized tertiary radical involved iodine see: b.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.