THE REDUCTION OF STEROID 2-ALPHA-FLUORO 4-EN-3-ONES
THE REDUCTION OF STEROID 2-ALPHA-FLUORO 4-EN-3-ONES
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DOI：
10.1021/jo00248a028
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发表时间：
1988-06-24
影响因子：
3.6
通讯作者：
ORR, JC
中科院分区：
文献类型：
--
作者：
GONDOS, G;MCGIRR, LG;ORR, JC
Reduction of testosterone with potassium tri-(R,S)-sec-butylborohydride gives predominantly the allylic 3.beta.-alcohol, while 2.alpha.-fluorotestosterone is converted solely to 2.alpha.-fluoro-4-androstene-3.alpha.,17.beta.-diol, and 2.alpha.-fluoro-4-androstene-3,17-dione to 2.alpha.-fluoro-3.alpha.-hydroxy-4-androsten-17-one. Reduction of testosterone with (R,R)- or (S,S)-Rh-DIOP and dihydrosilanes give predominantly allylic alcohols, while with the same catalysts and monohydrosilanes no allylic alcohols are found, the 4-double bond being instead reduced. The chirality of the DIOP reagents contributes only to a minor extent to stereoselectivity of 3-ketone reduction.
