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Volumn 13, Issue 9, 2011, Pages 2244-2247

Iodo-carbocyclization of electron-deficient alkenes: Synthesis of oxindoles and spirooxindoles

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EID: 84941944744     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol2005243     Document Type: Article
Times cited : (108)

References (66)
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    • One reaction pathway involved a 1,4-addition of an iodine radical to the conjugated double bond followed by radical cyclization onto the aromatic ring. However, the following results seemed to be against this proposal in our case: (i) cyclization of 3a took place readily in the dark to afford 4a in a similar yield; (ii) addition of benzoquinone did not inhibit the reaction; (iii) although yield remained moderate, the cyclization of (Z)- and (E)- N -2-dimethyl- N -phenylbut-2-enamide was stereospecific affording two distinct diastereomers (cf. Supporting Information). For radical based cyclization to oxindoles, see
    • One reaction pathway involved a 1,4-addition of an iodine radical to the conjugated double bond followed by radical cyclization onto the aromatic ring. However, the following results seemed to be against this proposal in our case: (i) cyclization of 3a took place readily in the dark to afford 4a in a similar yield; (ii) addition of benzoquinone did not inhibit the reaction; (iii) although yield remained moderate, the cyclization of (Z)- and (E)- N -2-dimethyl- N -phenylbut-2-enamide was stereospecific affording two distinct diastereomers (cf. Supporting Information). For radical based cyclization to oxindoles, see: Teichert, A.; Jantos, K.; Harms, K.; Studer, A. Org. Lett. 2004, 6, 3477-3480
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.