以三氟化硼-乙醚配合物为催化剂,研究了亚胺与氨甲酰基硅烷的反应.考察了亚胺碳原子连接基团(乙基、异丙基、三氟甲基、苯乙烯基、苯基、呋喃基、噻吩基和吡啶基)对反应的影响,合成了几种α-氨基酰胺;当亚胺氮原子连接的烃基和氨甲酰基硅烷中氮原子连接的烃基为手性基团S-1-苯乙基和R-1-苯乙基时,得到了具有高度立体选择性的产物(非对映异构体比率为14:1),是一种不对称合成α-氨基酰胺的新方法.
参考文献
[1] | Lin Y S,Alper H.A Novel Approch for the One-Pot Preparation of α-Aminoamides by Pd-Catalyzed Double Carbohydroamination[J].Angew Chem Int Ed Engl,2001,40:779-781. |
[2] | Pick R,Bauer M,Kazmaier U,et al.Ammonia in Ugi Reactions-Four-Component versus Six-Component Couplings[J].Synlett,2005,(3):757-760. |
[3] | Katritzky A R,Kirichenko N,Regovoy B V,et al.Facile N-Derivatization of α-Amino Esters and Amides via Benzotriazolylmethyl Derivatives[J].J Org Chem,2003,68 (23):9088-9092. |
[4] | Sanchez L M,Lopez D,Vesely B A,et al.Almiramides A-C:Discovery and Development of New Class of Leishmaniasis Lead Compound[J].J Med Chem,2010,53(10):4187-4197. |
[5] | Domling A,Ugi I.Multicomponent Reactions with Isocyanides[J].Angew Chem Int Ed,2000,39:3168-3210. |
[6] | Marquarding D,Hoffmann P H,Ugi I.Stereoselective For-Component Condensations of α-Ferrocenylethylamine and Its Absolute Configuration[J].J Am Chem Soc,1970,92 (7):1969-1971. |
[7] | Julia H S,Thorsten B,Michael U,et al.Diversity Oriented Synthesis of Benzoxazoles and Benzothiazoles[J].Tetrahedron Lett,2007,48 (51):9030-9034. |
[8] | Nazaret C,Jacinte J D,Mavia G V.Synthesis of Pseudopoptidic[(5H)-6-oxodibenzo[b,f][1,5]diazocine-5-yl]arylgly Cinamides by an Ugi 4cc/Staudinger/aza-Wittig Sequence[J].Tetrahedron,2008,64 (9):2225-2232. |
[9] | Chen J X,Cunico R F.Synthesis of α-Ketoamides from a Carbamoylsilane and Acid Chlorides[J].J Org Chem,2004,69(16):5509-5511. |
[10] | Cunico R F,Motta A R.Addition of Carbamoylsilanes to Electrophilically Substituted Alkenes:Preparaton of Functionalized Tertiary Amides[J].Org Lett,2005,7 (5):771-774. |
[11] | CHEN Jianxin,WEN Xueshan.Reaction of Carbamoylsilane with Nitrone and Tautomerism of Product[J].Acta Chim Sin,2009,64(14):1709-1711 (in Chinese).陈建新,温雪山.氨甲酰基硅烷与硝酮的反应及产物的互变异构[J].化学学报,2009,67 (14):1709-1711. |
[12] | Cunico R F,Chen J X.On the Preparation of Carbamoylsilanes[J].Synth Commun,2003,33 (11):1963. |
[13] | Chen J X,Cunico R F.α-(Dimethylamino) amides from a Carbamoylsilane and Iminium Salts[J].Tetrahedron Lett,2002,43(47):8595-8597. |
[14] | Chen J X,Cunico R F.α-Aminoamides from a Carbamoylsilane and Aldehyde Imines[J].Tetrahedron Lett,2003,44(43):8025-8027. |
[15] | GUO Wenyan,YAO Yuan,CHEN Jianxin,et al.Asymmetric Synthesis of α-Aminoamides Derivatives[J].Chinese J Medicinal Chem,2013,23 (3):197-202 (in Chinese).郭文彦,姚远,陈建新,等.α-氨基酰胺衍生物的不对称合成[J].中国药物化学杂志,2013,23(3):197-202. |
[16] | Bandini M,Cozzi P G,Umani R A,et al.Diastereoselective Addition of Higher Order Cupratesand Zinc-Copper Reagents to Imines Derived from (S)-1-Phenylethylamine[J].Tetrahedron,1999,55(26):8103-8110. |
[17] | James M H.A Simple and Efficient Synthesis of Ethyl and Methyl Glyoxylate[J].Synth Commun,1984,14(1):83-87. |
[18] | Cunico R F.Aminooxycarbene Behavior of a Carbamoylsilane[J].Tetrahedron Lett,2001,42(16):2931-2932. |
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%