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One‐Pot Synthesis of Pyrrolo[1,2‐ a ]indoles by Chiral N ‐Triflyl Phosphoramide Catalyzed Friedel‐Crafts Alkylation of 4,7‐Dihydroindole with β , γ ‐Unsaturated α ‐Keto Esters
Author(s) -
Zeng Mi,
Zhang Wei,
You Shuli
Publication year - 2012
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201200759
Subject(s) - friedel–crafts reaction , chemistry , alkylation , catalysis , organic chemistry , enantioselective synthesis
Chiral N ‐triflyl phosphoramide was found an efficient catalyst for the enantioselective Friedel‐Crafts alkylation reaction of 4,7‐dihydroindole with β , γ ‐unsaturated α ‐keto esters. In the presence of 5 mol% of the optimized catalyst, various pyrrolo[1,2‐ a ]indoles were obtained in excellent enantioselectivity, moderate yields and up to 3:1 diastereoselectivity based on the one‐pot synthesis including the Friedel‐Crafts alkylation reaction and the subsequent p ‐benzoquinone oxidation.