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Volumn 63, Issue 12, 1998, Pages 3899-3904

Diastereomer-Differentiating Radical β-Addition to 4- Or 5-Methyl-2-[(2,4,6-triisopropylphenyl)sulfinyl]-2-cyclopentenones

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EID: 0001419201     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9721507     Document Type: Article
Times cited : (30)

References (45)
  • 35
    • 85034480594 scopus 로고    scopus 로고
    • note
    • Only the trans compounds were formed in all reactions. The final products were formed via hydrolysis of the boron enolates; see the Supporting Information. In the boron enolates, the bulky aryl substituent on the sulfinyl group would be arranged in a position opposite to the added alkyl group by avoiding the steric interaction, and hydrolysis of the boron enolates occurs from the side opposite to the aryl group to give the trans compounds; see also ref 3a.
  • 41
    • 85034479979 scopus 로고    scopus 로고
    • note
    • 20c
  • 45
    • 0006073827 scopus 로고
    • 4 was added to hydrolyze the boron enolate without addition of acetic acid, excess triethylborane generated vast numbers of radicals on exposure to a large amount of oxygen to give unidentified products probably derived from the unreacted compound (4S)-4a or (5S)-4b. Acetic acid is known to react with trialkylborane; see: Brown, H. C.; Murray, K. J. Am. Chem. Soc. 1959, 81, 4108.
    • (1959) J. Am. Chem. Soc. , vol.81 , pp. 4108
    • Brown, H.C.1    Murray, K.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.