Asymmetric Cyanation Reactions

作者: N.H. Khan , R.I. Kureshy , S.H.R. Abdi , H.C. Bajaj , A. Sadhukhan

DOI: 10.1016/B978-0-08-097774-4.00616-1

关键词:

摘要: The asymmetric cyanation across C C, O, and N bonds ranks among the most important well-studied reactions in catalysis to achieve useful chiral building blocks for pharmaceuticals, agrochemicals, specialty materials. reaction demands careful selection of a catalyst cyanide source. A number efficient successful synthetic strategies have been developed that include cyanation-utilizing enzyme, organocatalyst, metal complexes as catalysts. As concern source cyanide, inorganic cyanides, example, NaCN KCN; organic trimethylsilyl alkyl cyanoformates, acetone cyanohydrin, acetyl cyanophosphorylates, etc. employed, depending upon targeted substrates. Since subject is vast, this chapter discusses detail chiral-metal-complex-based catalytic synthesis cyanohydrins using different sources. An attempt made discuss mechanism involved enantioselective reactions.

参考文章(235)
Otto Meth-Cohn, Alan R. Katritzky, Charles W. Rees, Comprehensive organic functional group transformations II Pergamon , Elsevier Science. ,(1995)
Jun-ichi Oku, Naofumi Ito, Shohei Inoue, Asymmetric cyanohydrin synthesis catalyzed by synthetic dipeptides, 2 Macromolecular Chemistry and Physics. ,vol. 183, pp. 579- 586 ,(1982) , 10.1002/MACP.1982.021830307
A. Schmid, J. S. Dordick, B. Hauer, A. Kiener, M. Wubbolts, B. Witholt, Industrial biocatalysis today and tomorrow Nature. ,vol. 409, pp. 258- 268 ,(2001) , 10.1038/35051736
Chun-Wei Chang, Chun- TzuYang, Chyuan-Der Hwang, Biing-Jiun Uang, 1,2-Diphenylethylenediamine linked chiral Ti(IV) complex—a new entry to the highly enantioselective silylcyanation of aliphatic and aromatic aldehydes Chemical Communications. pp. 54- 55 ,(2002) , 10.1039/B107867D
Carlos Baleizão, Bárbara Gigante, Hermenegildo Garcia, Avelino Corma, Ionic liquids as green solvents for the asymmetric synthesis of cyanohydrins catalysed by VO(salen) complexes Green Chemistry. ,vol. 4, pp. 272- 274 ,(2002) , 10.1039/B201497C
Biswajit Saha, T. V. RajanBabu, Nickel(0)-Catalyzed Asymmetric Hydrocyanation of 1,3-Dienes Organic Letters. ,vol. 8, pp. 4657- 4659 ,(2006) , 10.1021/OL062002F
Carlos Baleizão, Bárbara Gigante, Hermenegildo Garcia, Avelino Corma, Vanadyl salen complexes covalently anchored to an imidazolium ion as catalysts for the cyanosilylation of aldehydes in ionic liquids Tetrahedron Letters. ,vol. 44, pp. 6813- 6816 ,(2003) , 10.1016/S0040-4039(03)01746-5
Noor-ul H. Khan, Santosh Agrawal, Rukhsana I. Kureshy, Sayed H.R. Abdi, Vishal J. Mayani, Raksh V. Jasra, Easily recyclable polymeric V(V) salen complex for the enantioselective O-acetyl cyanation of aldehydes Journal of Molecular Catalysis A-chemical. ,vol. 264, pp. 140- 145 ,(2007) , 10.1016/J.MOLCATA.2006.09.009
Ángeles Gama, Lucı́a Z. Flores-López, Gerardo Aguirre, Miguel Parra-Hake, Ratnasamy Somanathan, Thomas Cole, A study of substituent effects on the enantioselective trimethylsilylcyanation of benzaldehyde catalyzed by chiral Schiff base–titanium(IV) complexes Tetrahedron-asymmetry. ,vol. 16, pp. 1167- 1174 ,(2005) , 10.1016/J.TETASY.2005.01.030
Maria I Monterde, Serge Nazabadioko, Francisca Rebolledo, Rosario Brieva, Vicente Gotor, Chemoenzymatic synthesis of azacycloalkan-3-ols Tetrahedron-asymmetry. ,vol. 10, pp. 3449- 3455 ,(1999) , 10.1016/S0957-4166(99)00351-1