Literature DB >> 20161011

New Approach to 4-Phenyl-β-aminotetralin from 4-(3-Halophenyl)tetralen-2-ol Phenylacetate.

Adam S Vincek1, Raymond G Booth.   

Abstract

Mixed trifluoroacetyl phenylacetyl anhydride and 3-halostyrenes (fluoro, chloro, and bromo) or vinylcycloalkanes (cyclohexyl, cyclooctyl), undergo cascade Friedel-Crafts cycli-acylalkylation, enolization, and O-acylation to give 4-substituted tetralen-2-ol phenylacetates, without additional solvent in good yields. Base alcoholysis of 4-phenyltetralen-2-ol phenylacetate reveals the tetral-2-one for asymmetric transfer hydrogenation. Bromophenyltetralen-2-ol phenylacetate undergoes Suzuki coupling, and provides a short route to trans-4-phenyl-β-aminotetralin.

Entities:  

Year:  2009        PMID： 20161011      PMCID： PMC2758692          DOI： 10.1016/j.tetlet.2009.06.099

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  11 in total

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  8 in total

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