New chiral ferrocenyl P,S-ligands for highly diastereo-/enantioselective catalytic [3 + 2] cycloaddition of azomethine ylides with cyclic and acyclic enones.
New chiral ferrocenyl P,S-ligands for highly diastereo-/enantioselective catalytic [3 + 2] cycloaddition of azomethine ylides with cyclic and acyclic enones.
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DOI：
10.1021/ol1024647
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发表时间：
2010-12
期刊：
影响因子：
5.2
通讯作者：
Cheng Zhang;Sai-Bo Yu;Xiangping Hu;Dao‐Yong Wang;Zhuo Zheng
中科院分区：
文献类型：
--
作者：
Cheng Zhang;Sai-Bo Yu;Xiangping Hu;Dao‐Yong Wang;Zhuo Zheng
开发了一类新的手性二茂铁基P，S配体，并成功地应用于甲亚胺叶立德与各种烯酮的高内选择性催化不对称环加成反应，包括环状和非环状α-烯酮。对于环状α-烯酮，[Cu(CH(3)CN)(4)]ClO(4)/(R(C)，S(Fc))-2f络合物催化环加成反应得到唯一的对映选择性良好的内环加成产物(通常为99%ee)，而AgOAc/(R(C)，S(Fc))-2f催化体系对开环α-烯酮表现出良好的内/外选择性(endo/exo=91/9~96/4)和较高的对映控制(高达98%ee)。
A new family of chiral ferrocenyl P,S-ligands has been developed and successfully applied in a highly endo-selective catalytic asymmetric cycloaddition of azomethine ylides with various enones, including cyclic and acyclic α-enones. For cyclic α-enones, a [Cu(CH(3)CN)(4)]ClO(4)/(R(c),S(Fc))-2f complex catalyzed the cycloaddition to give the sole endo-cycloadducts in perfect enantioselectivities (normally 99% ee), while an AgOAc/(R(c),S(Fc))-2f catalytic system exhibited good endo/exo selectivities (endo/exo = 91/9 to 96/4) and high enantiocontrol (up to 98% ee) for acyclic α-enones.