A New Class of Planar-Chiral Ferrocenes: Serendipitous Formation of 1,2-Ferrocenediylazaphosphinines
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- 作者：Geun-Ho Hwang ; Eun-Sook Ryu ; Dong-Kyu Park ; Sang Chul Shim ; Chan Sik Cho ; Tae-Jeong Kim ; Jong Hwa Jeong ; and Minserk Cheong
- 刊名：Organometallics
- 出版年：2001
- 出版时间：December 24, 2001
- 年：2001
- 卷：20
- 期：26
- 页码：5784 - 5787
- 全文大小：55K
- 年卷期：v.20,no.26(December 24, 2001)
- ISSN：1520-6041
文摘
The reaction of 1-(
-aminoalkyl)-2-diphenylphosphinoferrocene (1) with glyoxals gave via an unusual heterocyclization 1,2-ferrocenediylazaphosphinines(3) as a new class of planar-chiral ferrocenes. Theproducts were fully characterized by analytical andvarious spectroscopic techniques. In particular, a complete assignment of all protons and carbons was madeby various NMR techniques. A substantial degree of
-electron delocalization extending over the fused heterocyclic ring can be evidenced by IR and UV/vis spectraand in the case of 3a by X-ray crystallographic data.Employment of rac-3a as ligand for Cu-catalyzed cyclopropanation of styrene by ethyl diazoacetate revealed acomplete diastereo-discrimination leading to the formation of trans-product in 100% yield.
-aminoalkyl)-2-diphenylphosphinoferrocene (1) with glyoxals gave via an unusual heterocyclization 1,2-ferrocenediylazaphosphinines(3) as a new class of planar-chiral ferrocenes. Theproducts were fully characterized by analytical andvarious spectroscopic techniques. In particular, a complete assignment of all protons and carbons was madeby various NMR techniques. A substantial degree of-electron delocalization extending over the fused heterocyclic ring can be evidenced by IR and UV/vis spectraand in the case of 3a by X-ray crystallographic data.Employment of rac-3a as ligand for Cu-catalyzed cyclopropanation of styrene by ethyl diazoacetate revealed acomplete diastereo-discrimination leading to the formation of trans-product in 100% yield.