Lewis‐Acid‐Catalyzed Intramolecular Aza‐Friedel–Crafts Reaction of  N‐tert‐ Butanesulfinyl Imines: Efficient Synthesis of Optically Active 9‐Aminofluorene Derivatives | Zendy

Li Yi | Zendy; Xu MingHua | Zendy

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Lewis‐Acid‐Catalyzed Intramolecular Aza‐Friedel–Crafts Reaction of N‐tert‐ Butanesulfinyl Imines: Efficient Synthesis of Optically Active 9‐Aminofluorene Derivatives

Author(s) -

Li Yi,

Xu MingHua

Publication year - 2013

Publication title -

asian journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.846

H-Index - 44

eISSN - 2193-5815

pISSN - 2193-5807

DOI - 10.1002/ajoc.201200161

Subject(s) - chemistry , intramolecular force , friedel–crafts reaction , optically active , diastereomer , catalysis , lewis acids and bases , frustrated lewis pair , combinatorial chemistry , alkylation , organic chemistry

Am‐aza‐ing ! An efficient and straightforward method for the construction of optically active 9‐aminofluorenes by a Lewis acid (LA)‐catalyzed asymmetric intramolecular aza‐Friedel–Crafts alkylation of N ‐ tert ‐butanesulfinyl imines has been developed. The reaction can be accomplished with ease in the presence of a catalytic amount of Bi(OTf) 3 at room temperature to give the desired products in good yields and up to 96:4 diastereomeric ratio.

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