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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.