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Synlett 1996; 1996(11): 1071-1075
DOI: 10.1055/s-1996-5662
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New Strategies Towards Asymmetric 1-Aminocyclopropanecarboxylic Acids: Alkylation and SN’ Cyclization of (4S)-1-Chloropent-2-en-4-ol Derivatives by (N-diphenylmethyleneamino)acetonitrile

Philippe Dorizon, 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 41 62 78, E-mail jasalaun@icmo.u-psud.fr
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Publication Date:
31 December 2000 (online)

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Palladium(0) catalyzed alkylation of (4S)-1-chloropent-2-en-4-ol 7a by the anion of N-(diphenylmethyleneamino)acetonitrile 2, followed by SN’ cyclization under Mitsunobu conditions (DEAD, Me3P), produced diastereoselectively the (1S,2S)-1-amino-2-(prop-1-enyl) cyclopropanecarbonitrile 9 (de = 88%), a suitable precursor of asymmetric ACCs.

Palladium(0) catalyzed alkylation, and SN’ cyclization under Mitsunobu conditions