Professor Michael North

Professor of Organic Chemistry and joint director of the URC in Catalysis and Intensified Processing

 

Catalytic Asymmetric Cyanohydrin Synthesis

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1.        M. North, 'A Conformational Study on Cyclo[(S)-Phenylalanyl-(S)-Histidyl] by Molecular Modelling and NMR Techniques.' Tetrahedron, 1992, 48, 5509-5522.

 

2.        D.J.P. Hogg and M. North, 'Mechanistic Studies on the Asymmetric Addition of HCN Aldehydes Catalysed by Cyclo[(S)-His-(S)-Phe].' Tetrahedron, 1993, 49, 1079-1090.

 

3.        M.North and D.J.P. Hogg, 'A Conformational Study on Cyclo[(S)-His-(S)-Phe] by Molecular Modelling and NMR Techniques.' in 'Peptides 1992' Escom, 1993, 949-950.

 

4.        D.J.P. Hogg, M. North, R.B. Stokoe, and W.G. Teasdale; 'The Oxidation of Benzaldehyde to Benzoic Acid Catalysed by Cyclo-[(S)-His-(S)-Phe], and its Implications for the Catalytic Asymmetric Addition of HCN to Aldehydes', Tetrahedron Asymmetry, 1993, 4, 1553-1558.

 

5.        D.J.P. Hogg, M. North, and R.B. Stokoe; 'A Conformational Comparison of Cyclo-[(S)-His-(S)-Leu] and Cyclo-[(S)-His-(S)-Phe], Catalysts for the Asymmetric Addition of HCN to Aldehydes', Tetrahedron, 1994, 50, 7933-7946.

 

6.        D. Apperley, M. North, and R.B. Stokoe; 'The Catalytically Active Conformation of Cyclo-[(S)-His-(S)-Phe] as Determined by Solid State NMR', Tetrahedron Asymmetry, 1995, 6, 1869-1872.

 

7.        Y. Belokon', N. Ikonnikov, M. Moscalenko, M. North, S. Orlova, V. Tararov, and L. Yashkina; 'Asymmetric Trimethylsilylcyanation of Aldehydes Catalyzed by Chiral (Salen)Ti(IV) Complexes', Tetrahedron Asymmetry, 1996, 7, 851-855.

 

8.        Y. Belokon', M. Flego, N. Ikonnikov, M. Moscalenko, M. North, C. Orizu, V. Tararov, and M. Tasinazzo; 'Asymmetric Addition of TMSCN to Aldehydes Catalysed by Chiral (Salen)Ti(IV) Complexes', J. Chem. Soc., Perkin Trans. 1, 1997, 1293-1295.

 

9.        Y.N. Belokon', L.V. Yashkina, M.A. Moscalenko, A.A. Chesnokov, V.S. Kublitsky, N.S. Ikonnikov, S.A. Orlova, V.I. Tararov, and M. North; 'Asymmetric trimethylsilylation of aldehydes catalyzed by chiral salen TiIV complexes with the C1 symmetry', Izvestiya Akademii Nauk. Seriya Khimicheskaya, 1997, 2040: Translated as Russian Chem. Bull., 1997, 46, 1936-1938.

 

10.     V.I. Tararov, D.E. Hibbs, M.B. Hursthouse, N.S. Ikonnikov, K.M.A. Malik, M. North, C. Orizu, and Y.N. Belokon'; 'First structurally defined catalyst for the asymmetric addition of trimethylsilyl cyanide to benzaldehyde', Chem. Commun., 1998, 387-388.

 

11.     Y.N. Belokon’, S. Caveda-Cepas, B. Green, N.S. Ikonnikov, V.N. Khrustalev, V.S. Larichev, M.A. Moscalenko, M. North, C. Orizu, V.I. Tararov, M. Tasinazzo, G.I. Timofeeva, and L.V. Yashkina; ‘The Asymmetric Addition of Trimethylsilyl Cyanide to Aldehydes Catalysed by Chiral (Salen)Titanium Complexes’, J. Am. Chem. Soc., 1999, 121, 3968-3973.

 

12.     V.I. Tararov, C. Orizu, N.S. Ikonnikov, V.S. Larichev, M.A. Moscalenko, L.V. Yashkina, M. North, and Y.N. Belokon ’Effects of the temperature and substituents in chiral Ti-IV(salen) catalysts on the enantioselectivity of the addition of Me3SiCN to PhCHO’, Russ. Chem. Bull., 1999, 48, 1128-1130.

 

13.     Y.N. Belokon’, B. Green, N.S. Ikonnikov, M. North, and V.I. Tararov; ‘The Asymmetric Addition of Trimethylsilyl Cyanide to Ketones Catalysed by a Bimetallic Chiral (Salen)Titanium Complex’, Tetrahedron Lett., 1999, 40, 8147-8150.

 

14.     Y.N. Belokon’, B. Green, N.S. Ikonnikov, V.S. Larichev, B.V. Lokshin, M.A. Moscalenko, M. North, C. Orizu, A.S. Peregudov, and G.I. Timofeeva; ‘Mechanistic Investigation of the Asymmetric Addition of Trimethylsilyl Cyanide to Aldehydes Catalysed by Dinuclear Chiral (Salen)Titanium Complexes.’ Eur. J. Org. Chem., 2000, 2655-2661.

 

15.     Y.N. Belokon’, M. North, and T. Parsons; ‘Vanadium catalysed asymmetric cyanohydrin synthesis’ Org. Lett., 2000, 2, 1617-1619.

 

16.     Y.N. Belokon’, B. Green, N.S. Ikonnikov, M. North, T. Parsons and V.I. Tararov; ‘Optimized Catalysts for the Asymmetric Addition of Trimethylsilyl Cyanide to Aldehydes and Ketones’ Tetrahedron, 2001, 57, 771-779.

 

17.     Y.N. Belokon, A.V. Gutnov, M.A. Moskalenko, L.V. Yashkina, D.E. Lesovoy, N.S. Ikonnikov, V.S. Larichev, and M. North; ‘Catalytic Asymmetric Synthesis of O-Acetyl Cyanohydrins from KCN, Ac2O and Aldehydes’ Chem. Commun., 2002, 244-245.

 

18.     Y.N. Belokon, P. Carta, A.V. Gutnov, V. Maleev, M.A. Moskalenko, L.V. Yashkina, N.S. Ikonnikov, N. V. Voskoboev, V.N. Khrustalev, and M. North; ‘Catalytic Asymmetric Synthesis of O-Acetylcyanohydrins from Potassium Cyanide, Acetic Anhydride, and Aldehydes Promoted by Chiral Salen Complexes of Titanium(IV) and Vanadium(V)’, Helv. Chim. Acta, 2002, 85, 3301-3312.

 

19.     Y.N. Belokon’, A.J. Blacker, L.A. Clutterbuck and M. North; ‘Catalytic, Asymmetric Synthesis of Cyanohydrin Ethyl Carbonates’ Org. Lett., 2003, 5, 4505-4507.

 

20.     Y.N. Belokon’, P. Carta and M. North; ‘Catalytic, asymmetric synthesis of cyanohydrin esters: The effect of anhydride structure on enantioselectivity’ Lett. Org. Chem. 2004, 1, 81-83.

 

21.     Y.N. Belokon, M. North, V.I. Maleev, N.V. Voskoboev, M.A. Moskalenko, A.S. Peregudov, A.V. Dmitriev, N.S. Ikonnikov, and H.B. Kagan; ‘In Situ Formation of a Heterobimetallic Chiral [(Salen)TiIV]/ [(Salen)VV] Catalyst for the Asymmetric Addition of TMSCN to Benzaldehyde’ Angew. Chem. Int. Ed. Engl. 2004, 43, 4085-4089.

 

22.     M. North, A.W. Parkins and A.N. Shariff; ‘Catalytic, asymmetric synthesis of a-acetoxy amides’ Tetrahedron Lett. 2004, 45, 7625-7627.

 

23.     Y.N. Belokon’, A.J. Blacker, P. Carta, L.A. Clutterbuck, and M. North; ‘Synthetic and mechanistic studies on asymmetric cyanohydrin synthesis using a titanium(salen) bimetallic catalyst’ Tetrahedron, 2004, 60, 10433-10447.

 

24.     Y.N. Belokon, A.G. Bulychev, V.I. Maleev, M. North, I.L. Malfanov, and N.S. Ikonnikov; ‘Asymmetric synthesis of cyanohydrins catalysed by a potassium D-bis[N-salicylidene-(R)-tryptophanato]cobaltate complex’ Mendeleev Commun., 2004, 249-250.

 

25.     Y.N. Belokon’, P. Carta, and M. North; ‘Asymmetric Synthesis of Polymer-Supported Cyanohydrin Acetates’ Tetrahedron Lett. 2005, 46, 4483-4486.

 

26.     Y.N. Belokon, E. Ishibashi, H. Nomura, and M. North; ‘Cyanide Ion Cocatalysis in Ti(salen) Catalysed Asymmetric Cyanohydrin Carbonate Synthesis’ Chem Commun. 2006, 1775-1777.

 

27.     Y.N. Belokon, V.I. Maleev, I.L. Mal’fanov, T.F. Savel’eva, N.S. Ikonnikov, A.G. Bulychev, D.L. Usanov, D.A. Kataev, and M. North; ‘Anionic chiral cobalt(III) complexes as catalysts for the asymmetric synthesis of cyanohydrins’ Russian Chemical Bulletin, Int. Ed. 2006, 55, 821-827. Translated from Izvestiya Akademii Nauk. Seriya Khimicheskaya 2006, 793-799.

 

28.     Y.N. Belokon, A.J. Blacker, L.A. Clutterbuck, D. Hogg, M. North, and C. Reeve; ‘An Asymmetric, Chemo-Enzymatic Synthesis of O-Acetylcyanohydrins’ Eur. J. Org. Chem. 2006, 4609-4617.

 

29.     Y.N. Belokon, D. Chusov, D.A. Borkin, L.V. Yashkina, A.V. Dmitriev, D. Katayev, and M. North; ‘Chiral Ti(IV) complexes of hexadentate Schiff bases as precatalysts for the asymmetric addition of TMSCN to aldehydes and the ring opening of cyclohexane oxide’ Tetrahedron: Asymmetry 2006, 17, 2328-2333.

 

30.     Y.N. Belokon, V.I. Maleev, M. North, and D.L. Usanov; ‘V(salen)X catalysed asymmetric cyanohydrin synthesis: an unexpected influence of the nature of anion X on the catalytic activity of the complexes’ Chem Commun. 2006, 4614-4616.

 

31.     Y.N. Belokon, W. Clegg, R.W. Harrington, C. Young, and M. North; ‘Asymmetric cyanohydrin synthesis using heterobimetallic catalysts obtained from titanium and vanadium complexes of chiral and achiral salen ligands’ Tetrahedron 2007, 63, 5287-5299.

 

32.     Y.N. Belokon’, W. Clegg, R.W. Harrington, E. Ishibashi, H. Nomura and M. North; ‘Enantioselective and  Diastereoselective Syntheses of Cyanohydrin Carbonates’ Tetrahedron 2007, 63, 9724-9740.

 

33.        Y.N. Belokon´, V.I. Maleev, D.A. Kataev, I.L. Mal´fanov, A.G. Bulychev, M.A Moskalenko, T.F.Saveleva, T.V. Skrupskaya, K.A. Lyssenko, I.A. Godovikov, and M. North; ‘Potassium and silver chiral cobaltate(iii) complexes as precatalysts for asymmetric C-C bond formation’ Tetrahedron: Asymmetry 2008, 19, 822-831.

 

34.     Y.N. Belokon’, W. Clegg, R.W. Harrington, M. North and C. Young; ‘In situ formation of heterobimetallic salen complexes containing titanium and/or vanadium ions’ Inorg. Chem. 2008, 47, 3801-3814.

 

35.     Y.N. Belokon', J. Hunt and M. North; ‘TitaniumIV(salen) and vanadiumV(salen) complexes derived from C2- and C1-symmetric diamines for asymmetric cyanohydrin synthesis’ Synlett 2008, 2150-2154.

 

36.     Y.N. Belokon', J. Hunt and M. North ‘Asymmetric catalysis of carbon-carbon bond forming reactions using amino acid derived C1-symmetrical salen ligands’ Tetrahedron: Asymmetry 2008, 19, 2804-2815.

 

37.     Y.N. Belokon, D. Chusov, T. Skrupskaya, D. Borkin, L.V. Yashkina, K.A. Lyssenko, M.M. Il`in, T. Strelkova, G.I. Timofeeva, A.S. Peregudov, M. North; ‘Synthesis of сhiral polydentate ligands and their application as precatalysts for the asymmetric addition of TMSCN to benzaldehyde’ Russian Chemical Bulletin. 2008, 57, 1981-1988.

 

38.     Y.N. Belokon, W. Clegg, R.W. Harrington, V.I. Maleev, M. North, M. Omedes Pujol, D.L. Usanov and C. Young; ‘Mechanism-guided development of VO(salen)X complexes as catalysts for the asymmetric synthesis of cyanohydrin trimethylsilyl ethers’ Chem. Eur. J. 2009, 15, 2148-2165.

 

39.     M. North and C. Williamson ‘A bimetallic aluminium(salen) complex for asymmetric cyanohydrin synthesis’ Tetrahedron Lett. 2009, 50, 3249-3252.

 

40.     M. North and M. Omedes-Pujol ‘Catalytic, asymmetric cyanohydrin synthesis in propylene carbonate’ Tetrahedron Lett. 2009, 50, 4452-4454.

 

41.     Y.N. Belokon´, V.I. Maleev, D.A. Kataev, T.F. Saveleva, T.V. Skrupskaya, Yulia V. Nelyubina and M. North ‘Chiral ion pairs in catalysis: lithium salts of chiral metallocomplex anions as catalysts for asymmetric C-C bond formation’ Tetrahedron: Asymmetry 2009 20, 1746-1752.

 

42.     M. North, P. Villuendas and C. Williamson ‘Mechanistic comparison of aluminium based catalysts for asymmetric cyanohydrin synthesis’ Tetrahedron, 2010, 66, 1915-1924.

 

43.     V. Chechik, M. Conte, T. Dransfield, M. North, and M. Omedes-Pujol ‘Cyanogen formation during asymmetric cyanohydrin synthesis’ Chem. Commun. 2010, 46, 3372-3374.

 

44.     M. North, M. Omedes-Pujol, and C. Williamson ‘Investigation of Lewis Acid versus Lewis Base Catalysis in Asymmetric Cyanohydrin Synthesis’ Chem. Eur. J. 2010, 16, 11367–11375.

 

45.     M. North, and M. Omedes-Pujol ‘Kinetics and mechanism of vanadium catalysed asymmetric cyanohydrin synthesis in propylene carbonate’ Belstein J. Org. Chem. 2010, 6, 1043­–1055.

 

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