Diastereomer-differentiating radical β-addition to 4- or 5-methyl-2-[(2,4,6-triisopropylphenyl)sulfinyl]-2-cyclopentenones

被引:30
作者
Mase, N [1 ]
Watanabe, Y [1 ]
Toru, T [1 ]
机构
[1] Nagoya Inst Technol, Dept Appl Chem, Showa Ku, Nagoya, Aichi 4668555, Japan
关键词
D O I
10.1021/jo9721507
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Addition of alkyl radicals to a diastereomeric mixture of(4R)- and (4S)-4-methyl-2-[(2,4,6-triisopropylphenyl)sulfinyl]-2-cyclopentenones gave the diastereomerically pure addition product derived from the (4R)-isomer, while the (4S)-isomer remained unreacted. The tel tert-butyl radical addition to a diastereomeric mixture of (5R)- and (5S)-5-methyl-2-[(2,4,6-triisopropylphenyl)sulfinyl]-2- cyclopentenones also gave the diastereomerically pure addition product. These results show that (4R) and (4S) or (5R) and (5S) diastereomers were kinetically separated in the radical beta-addition. The 1,2- and 1,3-steric interactions in the radical addition to 4- or 5-methyl-2-cyclopentenones were also examined.
引用
收藏
页码:3899 / 3904
页数:6
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