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Both isomers are in equilibrium in dichloromethane solution, the equilibrium constant being affected by the temperature in such a way that when the temperature increases, the relative concentration of the oxygen-bonded isomer 3-O increases. The homologue aqua-complex of iridium, (SIr,RC)-[Cp*Ir\u00ad{(R)-Prophos}\u00ad(OH2)]\u00ad[SbF6]2 (2), also reacts with MTNS; but only the sulfur-coordinated isomer (SIr,RC)-[Cp*Ir\u00ad{(R)-Prophos}\u00ad(\u03ba1S-MTNS)]2+ (4-S) is detected in the solution by NMR spectroscopy. The crystal structures of 3-S and 4-S have been elucidated by X-ray diffractometric methods. Complexes 1 and 2 catalyze the Friedel\u2013Crafts reaction of indole, N-methylindole, 2-methylindole, or N-methyl-2-methylindole with MTNS. Up to 93% ee has been achieved for N-methyl-2-methylindole. With this indole, the ee increases as conversion increases, ee at 263 K is lower than that obtained at 298 K, and the sign of the chirality of the major enantiomer changes at temperatures below 263 K. Detection and characterization of the catalytic intermediates metal-aci-nitro and the free aci-nitro compound as well as detection of the Friedel\u2013Crafts (FC)-adduct complex involved in the catalysis allowed us to propose a plausible double cycle that accounts for the catalytic observations.<\/jats:p>","DOI":"10.1021\/acsomega.0c03485","type":"journal-article","created":{"date-parts":[[2020,10,21]],"date-time":"2020-10-21T09:45:56Z","timestamp":1603273556000},"page":"27978-27989","source":"Crossref","is-referenced-by-count":7,"title":["Catalytic Enantioselective Alkylation of Indoles with\n                    <i>trans<\/i>\n                    -4-Methylthio-\u03b2-Nitrostyrene"],"prefix":"10.1021","volume":"5","author":[{"given":"Isabel","family":"Me\u0301ndez","sequence":"first","affiliation":[{"name":"Instituto de Si\u0301ntesis Qui\u0301mica y Cata\u0301lisis Homoge\u0301nea (ISQCH), CSIC\ue5f8Universidad de Zaragoza , , Pedro Cerbuna 12 , ,","place":["Zaragoza, Spain, 50009"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Carlos","family":"Ferrer","sequence":"additional","affiliation":[{"name":"Instituto de Si\u0301ntesis Qui\u0301mica y Cata\u0301lisis Homoge\u0301nea (ISQCH), CSIC\ue5f8Universidad de Zaragoza , , Pedro Cerbuna 12 , ,","place":["Zaragoza, Spain, 50009"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8845-0174","authenticated-orcid":true,"given":"Ricardo","family":"Rodri\u0301guez","sequence":"additional","affiliation":[{"name":"Instituto de Si\u0301ntesis Qui\u0301mica y Cata\u0301lisis Homoge\u0301nea (ISQCH), CSIC\ue5f8Universidad de Zaragoza , , Pedro Cerbuna 12 , ,","place":["Zaragoza, Spain, 50009"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8054-2237","authenticated-orcid":true,"given":"Fernando J.","family":"Lahoz","sequence":"additional","affiliation":[{"name":"Instituto de Si\u0301ntesis Qui\u0301mica y Cata\u0301lisis Homoge\u0301nea (ISQCH), CSIC\ue5f8Universidad de Zaragoza , , Pedro Cerbuna 12 , ,","place":["Zaragoza, Spain, 50009"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Pilar","family":"Garci\u0301a-Ordun\u0303a","sequence":"additional","affiliation":[{"name":"Instituto de Si\u0301ntesis Qui\u0301mica y Cata\u0301lisis Homoge\u0301nea (ISQCH), CSIC\ue5f8Universidad de Zaragoza , , Pedro Cerbuna 12 , ,","place":["Zaragoza, Spain, 50009"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4196-5856","authenticated-orcid":true,"given":"Daniel","family":"Carmona","sequence":"additional","affiliation":[{"name":"Instituto de Si\u0301ntesis Qui\u0301mica y Cata\u0301lisis Homoge\u0301nea (ISQCH), CSIC\ue5f8Universidad de Zaragoza , , Pedro Cerbuna 12 , ,","place":["Zaragoza, Spain, 50009"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2020,10,21]]},"reference":[{"key":"2026081417142171300_cit1","volume-title":"Comprehensive Asymmetric Catalysis","author":"Jacobsen","year":"1999"},{"key":"2026081417142171300_cit2a","doi-asserted-by":"crossref","DOI":"10.1002\/9783527618309","volume-title":"Lewis Acids in Organic Synthesis","author":"Yamamoto","year":"2000"},{"key":"2026081417142171300_cit2b","doi-asserted-by":"crossref","DOI":"10.1002\/9783527619405","volume-title":"Transition Metals for Organic Synthesis: Building Blocks and Fine\nChemicals","author":"Beller","year":"2004"},{"key":"2026081417142171300_cit3","doi-asserted-by":"publisher","first-page":"78","DOI":"10.1016\/j.jorganchem.2018.10.011","article-title":"Organometal-catalyzed\nasymmetric Friedel-Crafts reactions","volume":"879","author":"Heravi","year":"2019","journal-title":"J. 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