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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1998年 / 63卷 / 12期

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

页码：3899 / 3904

页数：6

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