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化学学报
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化学学报 ›› 1995, Vol. 53 ›› Issue (5): 501-508. 上一篇    下一篇

研究论文

甾体植物生长调节剂合成研究31: 甲烷磺酰胺对(22E)-甾体不饱和侧链的锇催化的不对称双羟化反应的影响

黄良富;胡琦颖;周维善;夏立钧;毕茂华   

  1. 中国科学院上海有机化学研究所
  • 发布日期:1995-05-15

Studies on steroidal plant-growth regulator 31: Effects of methanesulfonamide on the asymmetric osmylation of (22E)-steroidal unsaturated sidechains

HUANG LIANGFU;HU QIYING;ZHOU WEISHAN;XIA LIJUN;BI MAOHUA   

  • Published:1995-05-15

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本文报道甲烷磺酰胺用于油菜甾体不饱和侧链的锇催化的不对称双羟化反应。结果使具有 △^2^(^3^)化合物。例如8和12反应速度明显加快, 对映选择性未受明显影响。降低OsO~4及配体用量, 对映选择性和反应速度明显降低。比较几种不同配体, 表明两个易得的DHQD-PHN和DHQD-NAP是最好的配体。改进后的方法适宜于高立体选择性构成油菜甾体的侧链。

关键词: 催化, 植物生长调节剂, 锇, 不对称反应, 甲烷磺酰胺, 油菜甾体侧链, 生命有机国家重点实验室资助项目

The effects of methanesulfonamide on the asymmetric osmylation of (22E)-steriodal unsaturated sidechains have been studied with six examples. MeSO~2NH~2 can greatly enhance the rate of dihydroxylation in case there is another △^2^(^3^) double bond without effect of the enantioselectivity. However, the rate of reaction and stereoselectivity are decreased, the amounts of chiral ligand and osmium catalyst being diminished. Our improved method is very effective to construction of brassinosteroidal sidechains with DHQD-PHN and DHQD-NAP as chiral ligands.

Key words: CATALYSIS, PLANT GROWTH REGULATORS, OSMIUM

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