Asymmetric Palladium(0) Catalyzed Tandem Alkylation and SN′ Cyclization of 1,4-Dichlorobut-2-ene by Chiral Imines of Aminoacetonitrile for the Total Synthesis of 1-Aminocyclopropanecarboxylic Acids

Philippe Dorizon; Guifa Su; Guitte Ludvig; Lilyia Nikitina; Jean Ollivier; Jacques Salaün

doi:10.1055/s-1998-1687

Synlett 1998; 1998(5): 483-486
DOI: 10.1055/s-1998-1687

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Asymmetric Palladium(0) Catalyzed Tandem Alkylation and S_N′ Cyclization of 1,4-Dichlorobut-2-ene by Chiral Imines of Aminoacetonitrile for the Total Synthesis of 1-Aminocyclopropanecarboxylic Acids

Philippe Dorizon^* , Guifa Su, Guitte Ludvig, Lilyia Nikitina, Jean Ollivier, Jacques Salaün

^*Laboratoire des Carbocycles (Associé au CNRS), Institut de Chimie Moléculaire d'Orsay, Bât. 420, Université de Paris-Sud, 91405 Orsay, France; Fax (33)1 69 15 62 78; E-mail: jasalaun@icmo.u-psud.fr

Abstract

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Chiral imines (-)- and (+)-8a, prepared from aminoacetonitrile and (-)- or (+)-1-hydroxypinanones, reacted with E- and Z-1,4-dichlorobut-2-enes 1 in the presence of (S)- or (R)-BINAP palladium(0) complexes to produce the diastereoselectively pure 1-amino-2-vinylcyclopropane carbonitrile E-13a, suitable precursor of ACCs. However subsequent Pd(0) induced reversible ring opening of the vinylcyclopropane moiety seems responsible for the low enantiomeric excesses obtained (≤32% ee).

(-)- and (+)-1-hydroxypinanone aminoacetonitrile imines - E-1-amino-2-vinylcyclopropanecarbonitriles

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