手性联二萘酚衍生物催化的苯乙炔与苯甲醛不对称加成反应

1.泸州医学院药学院,泸州,646000

2.泸州医学院化学教研室,泸州,646000

3.泸州医学院化学教研室,泸州,646000

4.泸州医学院药学院,泸州,646000

基金项目: 四川省教育厅项目(07ZZ014) 四川省科技厅项目(2008JY0090;2008SZ0052) 四川省青年科技基金(2009-26-417)

Asymmetric Addition of Phenylacetylene and Benzaldehyde Catalyzed by Chiral 1,1'-Bi-2-naphthol Derivatives

以手性联二萘酚为原料,合成了3,3'位取代的手性联二萘酚衍生物,研究了该衍生物配体在二乙基锌存在下,催化苯乙炔与苯甲醛的不对称加成反应,产物的产率为73%,e.e.值为40%.研究结果表明,手性联二萘酚衍让物结构的微小变化导致催化产物构型的改变.

[1]	Moore D,Pu L.BINOL-catalyzed Highly Enantioselective Terminal Alkyne Additions to Aromatic Aldehydes[J].Org Lett,2002,4:1855-1857.
[2]	Gao G,Moore D,Xie R G,et al.Highly Enantioselective Phenylacetylene Additions to Both Aliphatic and Aromatic Aldehydes[J].Org Lett,2002,4:41434146.
[3]	Gao G,Xie R G,Pu L.Highly Enantioselective Alkyne Additions to Aldehydes in the Presence of 1,1 '-Bi-2-naphthol and Hexamethylphosphoramide[J].Proc Nat Acad Sri (USA),2004,101 (15):5417-5420.
[4]	Gao G,Wang Q,Yu X Q,et al.Highly Enantioselective Synthesis of γ-Hydroxy-α,β-acetylenic Esters by Asymmetric Alkyne Addition to Aldehydes[J].Angew Chem Int Ed,2006,45:122-125.
[5]	Wang Q,Chen X,Tao L,et al.[J].J Org Chem,2001,72:97-101.
[6]	Wang Q,Chen S Y,Yu X Q,et al.1,1 '-Binaphthyl Ligands with Bulky 3,3'-tertiaryalkyl Substituents for the Asymmetric Alkyne Addition to Aromatic Aldehydes[J].Tetrahedron,2007,63:4422-4428.

上一张下一张

计量

作者相关

文章评分