NORMANT, JEAN-FRANCOIS / Chemistry / Researchers

International Center for Scientific Research

Researchers

Chemistry / NORMANT, JEAN-FRANCOIS

normantccr.jussieu.fr

Position

Emeritus Professor at the University P.& M.Curie.Paris, Laboratoire de Chimie des Organoéléments.

Research interests

- Development of organocopper chemistry : copper acetylides in synthesis. Vinylcopper reagents by carbocupration of alkynes and their use in the synthesis of various ethylenic or bi-ethylenic substrates with pure E or Z configuration. Applications to the synthesis of pheromones.

- Catalytic use of copper salts in reactions of Grignard reagents. Diastereoselective synthesis of chiral alcohols and aldehydes from acetals and organocopper reagents.

- Carbenoid chemistry using gem halo-lithio compounds and their copper analogs. Organomanganese chemistry, synthesis of ketones.

- Organofluorine derivatives via vinylic fluorinated organometallics.

- Bismetallic reagents : by the "metalla-Claisen" reactions of vinyl-allyl zinc, or of allenyl allylzinc reagents, their use for the creation of linear systems, stereospecifically di- or tri-substituted,or of di- or tri-substituted cyclopropanes.

- Carbocyclization of w-ene or w-yne organozinc reagents : access to cyclopentanes which are stereoselectively substituted, to triquinanes ...

-Preparation of selectively substituted pyrolidines and piperidines(racemic and optically active) by intramolecular carbocyclizations .

- Enantioselective carbolithiation of phenyl alkenes,and cinnamic derivatives, creation of two vicinal homochiral carbons.

-Configurational stability of organozinc reagents (particularly benzylic and allenylic ones)

Prizes and awards

Prize : Fondation Van't Hoff (1967)

French Society of Chemistry (1963) : Adrian Prize and (1990) : Lebel Prize

Prizes of the Academy of Sciences in 1979 and 1987

Silver medal of the CNRS (1979)

Correspondant of the Académie des Sciences (1990)

Member of the Académie des Sciences (1993).

Centenary Lecturer (2000) Royal Society of Chemistry

Publications

- Diastereoselective carbometallation of vinyl metals, J. Org. Chem., 1994, 59, 4154- Simple organometallic reagents for the elaboration of more sophisticated ones and multistep synthesis, Chemtracks, Org. Chem., 1994, 7, 59.

- Chapter in " Organocopper reagents ", Ed. R.J.K. Taylor, Oxford University Press, 1994

- Intramolecular metallo ene-allene reactions in J. Org. Chem., 1995, 60, 863-871

- Asymmetric carbolithiation of cinnamyl derivatives, J. Am. Chem. Soc., 1995, 117, 8853

- Organobismetallic reagents in : Chemical Reviews, 1996, 96, 3241-3267

- Reactivity of sp2 organogembismetallics : Feature article in Synthesis, 1996, 1499-1508

- Chapter on carbometallation reactions in : " Metal catalyzed cross coupling reactions ", Ed. P.J. Stang, F. Diederich, Wiley-VCH, Oct 1997

- Enantioselective carbolithiation of cinnamyl acetals, J. Org. Chem., 1997, 62, 4898

- Chapter on Carbometallation in " Transition Metals for Organic Synthesis ",
M. Beller, C. Bolm Editors. Wiley 1998 p 514

-Preparation of 1,n-bimetallic reagents in " Organozinc reagents, a practical Approach " Ed. by P. -Knochel and P. Jones Oxford University Press 1999 p 119

-First transfer of chirality in the Fritsch-Buttenberg-Wiechell rearrangement,via zinc carbenoids : a migration with retention of configuration I.Creton,H.Rezaei,I.Marek,J.F.Normant, Tetrahedron Lett., 1999, 40 , 1899-1902.

- Use of metallated allylic ethers for the elaboration of vicinally trisubstituted linear substrates or cyclopropyl carbinols, F.Ferreira, C.Herse, E.Riguet, J.F.Normant, Tetrahedron Lett.2000,41, 1733-1736.

- Regio- and enantioselective Carbolithiation of non activated C=C bonds. S.Norsikian, M. Baudry, J.F. Normant, Tetrahedron Lett.2000,41, 6575-6578.

-Preparation of 1-chloro,1,1-dibromo-,or 1,1-dichloroalkenes from ketones, H. Rezaei, J.F. Normant Synthesis, 2000, 109-112.

-Comparative study of the Diastereoselective Addition of Allenyl Zinc reagents to a -alkoxy Aldehydes and Imines. A straightforward synthesis of amino alcohols from imines. J. F. Poisson ,J. F. Normant ,J.Org. Chem., 2000, 65, 6553-6560.

-Diastereoselective carbozincation of propargylic amines, H.Rezaei, I. Marek, J.F. Normant,Tetrahedron, 2001, 57, 2477-2483.

-An easy access to enantioenriched ( a -substituted aldehydes by carbolithiation of ß–phenyl, or ß-silyl-(a ,ß-ethylenic aldehydes, protected with the monolithioamide of a chiral diamine.N.Brémand, P. Mangeney, J.F.Normant.Tetrahedron Lett. 2001, 42, 1883-1885.

-Configurational stability of propargyl Zinc Reagents. J-F Poisson, F. Chemla, J. F. Normant, Synlett, 2001, 305-307.

-Kinetic resolution of an organozinc reagent : in situ formation of an enantioenriched allenylzinc species.J.F. Poisson, J.F. Normant, J. Am. Chem. Soc. 2001, 123, 4639-4640.

-A configurationally stable alkoxyallenyl zinc reagent, en route to anti,anti-vicinal aminodiols. J.F. Poisson et J.F. Normant, Org. Lett. 2001, 3, 1889-1891.

-1,1-Dimetallic Reagents for the Elaboration of Stereoselectively di-, or trisubstituted Linear Substrates. J.F. Normant, Accounts of Chemical Research, 2001, 34, 640-644.

-Preparation of propargylic carbenoids and reaction with carbonyl compounds- A stereoselective synthesis of propargylic halohydrins and oxiranes. F. Chemla, N. Bernard, F.Ferreira, J.F. Normant, Eur. J. Org. Chem. 2001, 3295-3300.

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