{"user_id":"2DF688A6-F248-11E8-B48F-1D18A9856A87","oa":1,"date_updated":"2024-03-25T11:50:01Z","title":"Stereoselective formation of trisubstituted vinyl boronate esters by the acid-mediated elimination of α-hydroxyboronate esters","publication_identifier":{"eissn":["1520-6904"],"issn":["0022-3263"]},"publication_status":"published","doi":"10.1021/jo500773t","publication":"The Journal of Organic Chemistry","main_file_link":[{"open_access":"1","url":"https://doi.org/10.1021/jo500773t"}],"author":[{"first_name":"Weiye","last_name":"Guan","full_name":"Guan, Weiye"},{"last_name":"Michael","full_name":"Michael, Alicia Kathleen","id":"6437c950-2a03-11ee-914d-d6476dd7b75c","first_name":"Alicia Kathleen"},{"first_name":"Melissa L.","last_name":"McIntosh","full_name":"McIntosh, Melissa L."},{"first_name":"Liza","full_name":"Koren-Selfridge, Liza","last_name":"Koren-Selfridge"},{"full_name":"Scott, John P.","last_name":"Scott","first_name":"John P."},{"last_name":"Clark","full_name":"Clark, Timothy B.","first_name":"Timothy B."}],"extern":"1","date_created":"2024-03-21T07:58:31Z","month":"06","abstract":[{"lang":"eng","text":"The copper-catalyzed diboration of ketones followed by an acid-catalyzed elimination leads to the formation of 1,1-disubstituted and trisubstituted vinyl boronate esters with moderate to good yields and selectivity. Addition of tosic acid to the crude diboration products provides the corresponding vinyl boronate esters upon elimination. The trisubstituted vinyl boronate esters are formed as the (Z)-olefin isomer, which was established by subjecting the products to a Suzuki–Miyaura coupling reaction to obtain alkenes of known geometry."}],"article_type":"letter_note","citation":{"apa":"Guan, W., Michael, A. K., McIntosh, M. L., Koren-Selfridge, L., Scott, J. P., &#38; Clark, T. B. (2014). Stereoselective formation of trisubstituted vinyl boronate esters by the acid-mediated elimination of α-hydroxyboronate esters. <i>The Journal of Organic Chemistry</i>. American Chemical Society. <a href=\"https://doi.org/10.1021/jo500773t\">https://doi.org/10.1021/jo500773t</a>","short":"W. Guan, A.K. Michael, M.L. McIntosh, L. Koren-Selfridge, J.P. Scott, T.B. Clark, The Journal of Organic Chemistry 79 (2014) 7199–7204.","chicago":"Guan, Weiye, Alicia K. Michael, Melissa L. McIntosh, Liza Koren-Selfridge, John P. Scott, and Timothy B. Clark. “Stereoselective Formation of Trisubstituted Vinyl Boronate Esters by the Acid-Mediated Elimination of α-Hydroxyboronate Esters.” <i>The Journal of Organic Chemistry</i>. American Chemical Society, 2014. <a href=\"https://doi.org/10.1021/jo500773t\">https://doi.org/10.1021/jo500773t</a>.","mla":"Guan, Weiye, et al. “Stereoselective Formation of Trisubstituted Vinyl Boronate Esters by the Acid-Mediated Elimination of α-Hydroxyboronate Esters.” <i>The Journal of Organic Chemistry</i>, vol. 79, no. 15, American Chemical Society, 2014, pp. 7199–204, doi:<a href=\"https://doi.org/10.1021/jo500773t\">10.1021/jo500773t</a>.","ama":"Guan W, Michael AK, McIntosh ML, Koren-Selfridge L, Scott JP, Clark TB. Stereoselective formation of trisubstituted vinyl boronate esters by the acid-mediated elimination of α-hydroxyboronate esters. <i>The Journal of Organic Chemistry</i>. 2014;79(15):7199-7204. doi:<a href=\"https://doi.org/10.1021/jo500773t\">10.1021/jo500773t</a>","ieee":"W. Guan, A. K. Michael, M. L. McIntosh, L. Koren-Selfridge, J. P. Scott, and T. B. Clark, “Stereoselective formation of trisubstituted vinyl boronate esters by the acid-mediated elimination of α-hydroxyboronate esters,” <i>The Journal of Organic Chemistry</i>, vol. 79, no. 15. American Chemical Society, pp. 7199–7204, 2014.","ista":"Guan W, Michael AK, McIntosh ML, Koren-Selfridge L, Scott JP, Clark TB. 2014. Stereoselective formation of trisubstituted vinyl boronate esters by the acid-mediated elimination of α-hydroxyboronate esters. The Journal of Organic Chemistry. 79(15), 7199–7204."},"type":"journal_article","issue":"15","article_processing_charge":"No","volume":79,"oa_version":"Published Version","status":"public","date_published":"2014-06-10T00:00:00Z","_id":"15161","scopus_import":"1","language":[{"iso":"eng"}],"quality_controlled":"1","year":"2014","intvolume":"        79","page":"7199-7204","publisher":"American Chemical Society","keyword":["Organic Chemistry"],"day":"10"}