A modular synthesis of chiral aminoindanol-derived imidazolium salts
2008; Elsevier BV; Volume: 64; Issue: 29 Linguagem: Inglês
10.1016/j.tet.2008.03.072
ISSN1464-5416
AutoresJustin R. Struble, Jeffrey W. Bode,
Tópico(s)Synthetic Organic Chemistry Methods
ResumoA modular synthesis of N-substituted chiral imidazolium salts derived from (1R,2S)-(+)-1-amino-2-indanol is described. A wide range of amines are amenable to late stage introduction of the N-substituent to provide N-aryl, N-alkyl, and N-amino imidazolium salts, which serve as precursors to chiral N-heterocyclic carbenes (NHCs). A multi-gram synthesis of the N-mesityl derivative provides an important imidazolium salt for ongoing studies aimed at the development and understanding of NHC-catalyzed annulations. Critical to the success of this synthetic strategy is a chemoselective alkylation, 6-exo-tet ring closure of a formamide onto an epoxide, and a heterocyclic interconversion strategy.
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