Highly Diastereoselective Intermolecular β-Addition of Alkyl Radicals to Chiral 2-(Arylsulfinyl)-2-cycloalkenones

N Mase, Y Watanabe, Y Ueno…

Index: Mase, Nobuyuki; Watanabe, Yoshihiko; Ueno, Yoshio; Toru, Takeshi Journal of Organic Chemistry, 1997 , vol. 62, # 22 p. 7794 - 7800

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Citation Number: 56

Abstract

The diastereoselectivity of intermolecular β-addition of alkyl radicals to 2-(arylsulfinyl)-2- cycloalkenones depends largely upon the structure of the arylsulfinyl group. The reaction of 2-cyclopentenones or 2-cyclohexenones having a sterically bulky arylsulfinyl group such as (3, 5-di-tert-butyl-4-methoxyphenyl) sulfinyl,(2, 4, 6-triisopropylphenyl) sulfinyl or (2, 4, 6- trimethylphenyl) sulfinyl group gives 3-alkyl-2-(arylsulfinyl)-1-cyclopentanones or 3-alkyl-2 ...