Enantioselective platinum-catalyzed silicon-boron addition to 1,3-cyclohexadiene

Enantioselective platinum-catalyzed silicon-boron addition to 1,3-cyclohexadiene
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DOI:
10.1002/adsc.200505016
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发表时间:
2005-05-01
影响因子:
5.4
通讯作者:
Moberg, C
Moberg, C
中科院分区:
化学2区
文献类型:
--
作者:
Gerdin, M;Moberg, C

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在Pt(acac)(2)、DIBALH和由(S)-1,1 '-联-2-萘酚和二异丙基胺制备的亚磷酰胺存在下,1,3-环己二烯的硅硼化导致(1 R,4S)-1-(二甲基苯基硅基)4-(4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷-2-基)-2-环己烯,具有70%ee。基于Ni的手性催化剂不产生或基本上产生外消旋产物,而含Pd的配合物是无活性的。
Silaboration of 1,3-cyclohexadiene in the presence of Pt(acac)(2), DIBALH, and a phosphoramidite prepared from (S)-1,1'-bi-2-naphthol and diisopropylamine led to (1R,4S)-1-(dimethylphenylsilyl)4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-cyclohexene with 70% ee. Chiral catalysts based on Ni gave no or essentially racemic product, whereas complexes containing Pd were inactive.