Novel branched isocyanides as useful building blocks in the Passerini-amine deprotection-acyl migration (PADAM) synthesis of potential HIV-1 protease inhibitors

D Gravestock, AL Rousseau, ACU Lourens…

Index: Gravestock, David; Rousseau, Amanda L.; Lourens, Anna C.U.; Hoppe, Heinrich C.; Nkabinde, Lindiwe A.; Bode, Moira L. Tetrahedron Letters, 2012 , vol. 53, # 26 p. 3225 - 3229

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Abstract

Multi-component coupling reactions (MCRs) are a versatile means of obtaining complex molecules in a single step. 1 These reactions are extremely atom-efficient and often high-yielding. The Passerini MCR couples an aldehyde, a carboxylic acid and an isocyanide to yield a product containing a new stereogenic centre and both ester and amide functionalities (step a, Scheme 1). 2 An interesting variation of the Passerini three-component reaction has been reported, where the initial ...

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