Journal
ACS CATALYSIS
Volume 6, Issue 11, Pages 7641-7646Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.6b02080
Keywords
enantioselective catalysis; iridium; metal template; hydrogen bond formation; Friedel-Crafts alkylation; beta,beta-disubstituted nitroalkenes; indoles
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Funding
- National Natural Science Foundation of P. R. China [21272192, 21472154, 21572184]
- Fundamental Research Funds for the Central Universities [20720160027]
- National Thousand Talents Program of P. R. China
- 985 Program of the Chemistry and Chemical Engineering disciplines of Xiamen University
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A highly active catalyst for the enantioselective Friedel Crafts alkylation of indoles with beta,beta-disubstituted nitroalkenes is reported, allowing catalyst loadings down to 0.05 mol % for this challenging transformation, providing useful synthetic building blocks with an all carbon quaternary stereocenter. The catalyst is based on a biscyclometalated iridium(III) complex as a structural template, and through the ligand sphere it forms hydrogen bonds with the two substrates. Starting from a previous design (Angew. Chem. Int. Ed. 2013, 52, 14021), the catalyst was rendered C-2-symmetrical in order to maximize the atom economy of this catalyst scaffold (two catalytic centers per iridium complex), and, most importantly, rational design was applied to restrict the conformational freedom of a key hydrogen bond acceptor, being responsible for activating the indole nucleophile and bringing it in an ideal position for the presumed ternary transition state.
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