基于酸碱作用,将手性伯胺与质子酸原位结合制得有机小分子催化剂,并用于醛与醛的不对称Cross-aldol反应.与一般手性仲胺催化剂不同,该类伯胺催化剂得到的是顺式选择性构型的Cross-aldol产物,其产率达90%,顺反比和ee值分别为9∶1和90%.相比而言,采用简单易得的(1S,2S)-(+)-环己二胺即可得到较高选择性的顺式产物.
参考文献
[1] | Mahrwald R.Modem Aldol Reactions[M].Weinheim:WileyVCH,2004 |
[2] | Mahrwald R.Aldol Reactions[M].Heidelberg:Springer-Verlag,2009 |
[3] | List B.;Barbas CF.;Lerner RA. .Proline-catalyzed direct asymmetric aldol reactions[J].Journal of the American Chemical Society,2000(10):2395-2396. |
[4] | Berkessel A;Groger H.Asymmetric Organocatalysis[M].Weinheim:Wiley-VCH,2005 |
[5] | Dalko P I.Enantioselective Organocatalysis[M].Weinheim:Wiley-VCH,2007 |
[6] | Northrup A B;MacMillan D W C .[J].Journal of the American Chemical Society,2002,124:6798. |
[7] | Trost B M;Brindle C S .[J].Chemical Society Reviews,2010,39:1600. |
[8] | Kano, T;Yamaguchi, Y;Maruoka, K .A Designer Axially Chiral Amino Sulfonamide as an Efficient Organocatalyst for Direct Asymmetric anti-Selective Mannich Reactions and syn-Selective Cross-Aldol Reactions[J].Chemistry: A European journal,2009(27):6678-6687. |
[9] | Kano T;Yamaguchi Y;Tanaka Y;Maruoka K .[J].Angewandte Chemie International Edition,2007,46:1738. |
[10] | Li, J.;Fu, N.;Li, X.;Luo, S.;Cheng, J.-P. .Chiral primary-tertiary diamine-br?nsted acid salt catalyzed syn-selective cross-aldol reaction of aldehydes[J].The Journal of Organic Chemistry,2010(13):4501-4507. |
[11] | Luo S;Xu H;Li J;Zhang L Cheng J P .[J].Journal of the American Chemical Society,2007,129:3074. |
[12] | Mukherjee S;Yang J W;Hoffmann S;List B .[J].Chemical Reviews,2007,107:5471. |
[13] | Hayashi Y;Aratake S;Okano T;Takahashi J,Sumiya T,Shoji M .[J].Angewandte Chemie International Edition,2006,45:5527. |
上一张
下一张
上一张
下一张
计量
- 下载量()
- 访问量()
文章评分
- 您的评分:
-
10%
-
20%
-
30%
-
40%
-
50%