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Consequently, synthetically versatile \u03b1-allenyl tertiary alcohols are generally synthesized in two steps from ketones (e.g., Crabbe\u0301 homologation of propargylic alcohols) rather than by the direct addition of allenylation reagents to ketones. We have developed a regiospecific allenylation of ketones with isomerically pure propargyltrichlorosilane as an operationally simple, general method to prepare racemic monosubstituted \u03b1-allenyl tertiary alcohols. The method provided 29 \u03b1-allenyl tertiary alcohols in 8\u201399% isolated yields but it proved to be intolerant of ketones containing sterically large groups and enones.<\/jats:p>","DOI":"10.1021\/acs.joc.6c01070","type":"journal-article","created":{"date-parts":[[2026,8,4]],"date-time":"2026-08-04T14:33:47Z","timestamp":1785854027000},"page":"10896-10904","source":"Crossref","is-referenced-by-count":0,"title":["Regiospecific Allenylation\nof Ketones with Propargyltrichlorosilane"],"prefix":"10.1021","volume":"91","author":[{"ORCID":"https:\/\/orcid.org\/0009-0008-0406-7399","authenticated-orcid":true,"given":"Noble","family":"Brako","sequence":"first","affiliation":[{"name":"Florida Institute of Technology , , 150 West University Boulevard , , ,","place":["Melbourne, Florida, United States, 32901-6975"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Angela","family":"Coppola","sequence":"additional","affiliation":[{"name":"Florida Institute of Technology , , 150 West University Boulevard , , ,","place":["Melbourne, Florida, United States, 32901-6975"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tristan","family":"Dales","sequence":"additional","affiliation":[{"name":"Florida Institute of Technology , , 150 West University Boulevard , , ,","place":["Melbourne, Florida, United States, 32901-6975"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jada","family":"Hickerson","sequence":"additional","affiliation":[{"name":"Florida Institute of Technology , , 150 West University Boulevard , , ,","place":["Melbourne, Florida, United States, 32901-6975"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Turan","family":"Mienville","sequence":"additional","affiliation":[{"name":"Florida Institute of Technology , , 150 West University Boulevard , , ,","place":["Melbourne, Florida, United States, 32901-6975"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ava","family":"Storey","sequence":"additional","affiliation":[{"name":"Florida Institute of Technology , , 150 West University Boulevard , , ,","place":["Melbourne, Florida, United States, 32901-6975"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7272-5655","authenticated-orcid":true,"given":"Burjor","family":"Captain","sequence":"additional","affiliation":[{"name":"University of Miami , , 1301 Memorial Drive , , ,","place":["Coral Gables, Florida, United States, 33146-0431"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1137-1272","authenticated-orcid":true,"given":"Rajeev","family":"Prabhakar","sequence":"additional","affiliation":[{"name":"University of Miami , , 1301 Memorial Drive , , ,","place":["Coral Gables, Florida, United States, 33146-0431"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3542-1086","authenticated-orcid":true,"given":"Norito","family":"Takenaka","sequence":"additional","affiliation":[{"name":"Florida Institute of Technology , , 150 West University Boulevard , , ,","place":["Melbourne, Florida, United States, 32901-6975"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,8,3]]},"reference":[{"key":"2026081410095629900_cit1","doi-asserted-by":"publisher","first-page":"1063","DOI":"10.1351\/pac200880051063","article-title":"Golden opportunities in catalysis","volume":"80","author":"Krause","year":"2008","journal-title":"Pure Appl.\nChem."},{"key":"2026081410095629900_cit2a","doi-asserted-by":"publisher","first-page":"3074","DOI":"10.1002\/anie.201101460","article-title":"Allenes in Catalytic\nAsymmetric Synthesis and Natural Product Synthesis","volume":"51","author":"Yu","year":"2012","journal-title":"Angew. 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Chem."},{"key":"2026081410095629900_cit22c","doi-asserted-by":"publisher","first-page":"6392","DOI":"10.1021\/ja00128a043","article-title":"Selective\nFormation of Propargylsilanes and Allenylsilanes and Their Reactions\nwith Aldehydes for the Preparation of Homopropargylic and Allenic\nAlcohols","volume":"117","author":"Kobayashi","year":"1995","journal-title":"J. Am. Chem. Soc."},{"key":"2026081410095629900_cit22d","doi-asserted-by":"publisher","first-page":"323","DOI":"10.1002\/adsc.200505379","article-title":"Highly Selective\nPreparation of Allenic and Homopropargylic Hydrazides through Regiospecific\nAddition of Propargyltrichlorosilane and Allenyltrichlorosilane to\nVarious Types of N-Acylhydrazones","volume":"348","author":"Schneider","year":"2006","journal-title":"Adv. Synth. 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