Asymmetric synthesis. XVIII. Preparation of chiral 1,2-diamines via the CN(R,S) method. Application to the synthesis of an analog of tetraponerine

The reaction or organo-lithium or cuprate derivs. towards the cyano group of 2-cyano-6-phenyloxazolopiperidine synthon I gives an imine which is reduced to a primary amine with a remarkable stereoselectivity. An application of this reaction to the synthesis of the tetraponerine analog II is presented. [on SciFinder (R)]


Published in:
Tetrahedron Letters, 30, 38, 5137-40
Year:
1989
Keywords:
Note:
CAN 112:217324
31-5
Alkaloids
Inst. Chim. Subst. Nat.,CNRS,Gif-sur-Yvette,Fr.
Journal
0040-4039
written in English.
88056-92-2 Role: RCT (Reactant), RACT (Reactant or reagent) (butylation of); 126811-36-7P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and cyclization of, with glutaraldehyde); 126811-39-0P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and decyanation of); 126811-35-6P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and hydrogenolysis of); 126811-34-5P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and redn. of); 126811-37-8P; 126811-38-9P; 126811-40-3P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of); 111-30-8 (Glutaraldehyde) Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with (aminopentyl)piperidine)
Laboratories:




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