Tetrahedron

Pictet–Spengler/Palladium Catalyzed Allenylation and Carbonylation Processes

…, V Sridharan, S Suganthan, M Thornton-Pett, J Zhang

Index: Grigg; MacLachlan; MacPherson; Sridharan; Suganthan; Thornton-Pett; Zhang Tetrahedron, 2000 , vol. 56, # 35 p. 6585 - 6594

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Citation Number: 54

Abstract

The tactical combination of the Pictet–Spengler reaction with Pd catalyzed reactions with allene and with carbon monoxide provides rapid access to a range of tetrahydro-β-carboline and tetrahydroisoquinoline derivatives via intramolecular trapping of intermediate π-allyl– and acyl–palladium (II) complexes by the indolic or secondary amino moieties generating fused azepine and δ-lactam derivatives. Chiral tryptophan examples are also described.

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