Enantio- and Diastereoselective Synthesis of syn-β-Hydroxyallylsilanes via a Chiral (Z)-γ-Silylailylboronate

Enantio- and Diastereoselective Synthesis of syn-β-Hydroxyallylsilanes via a Chiral (Z)-γ-Silylailylboronate
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DOI:
10.1021/ol7018746
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发表时间:
2007-10-11
期刊:
影响因子:
5.2
通讯作者:
Roush, William R.
Roush, William R.
中科院分区:
化学1区
文献类型:
--
作者:
Lira, Ricardo;Roush, William R.

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使用试剂 14 和 15,通过 BF(3) 中心点 Et(2)O-促进的 γ-甲硅烷基烯丙基硼化反应制备通式结构 11 和 28 的顺式-β-羟基烯丙基硅烷,收率 50-86%,ee 91-95%(对于脂肪醛;对于苯甲醛,ee 50%)。
syn-beta-Hydroxyallylsilanes of general structure 11 and 28 are prepared in 50-86% yield and 91-95% ee (for aliphatic aldehydes; 50% ee for benzaldehyde) via the BF(3)center dot Et(2)O-promoted gamma-silylallylboration reactions, using reagents 14 and 15.