{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,22]],"date-time":"2026-10-22T01:39:50Z","timestamp":1792633190065,"version":"4.5.0"},"reference-count":18,"publisher":"MyJove Corporation","issue":"147","content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["JoVE"],"DOI":"10.3791\/59775","type":"journal-article","created":{"date-parts":[[2019,5,26]],"date-time":"2019-05-26T20:00:16Z","timestamp":1558900816000},"source":"Crossref","is-referenced-by-count":0,"title":["Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides"],"prefix":"10.3791","author":[{"given":"Tyler  J.","family":"Fulton","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Katherine  M.","family":"Townsend","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Michael  R.","family":"Krout","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"2098","published-online":{"date-parts":[[2019,5,26]]},"reference":[{"issue":"39","key":"ref1","doi-asserted-by":"crossref","first-page":"7295","DOI":"10.1039\/c0cc02309d","type":"journal-article","article-title":"Metal-Catalyzed Asymmetric Conjugate Addition Reaction: Formation of Quaternary Stereocenters","volume":"46","author":"Hawner","year":"2010","unstructured":"Hawner, C.; Alexakis, A. Metal-Catalyzed Asymmetric Conjugate Addition Reaction: Formation of Quaternary Stereocenters. Chemical Communications. 46 (39), 7295-7306 (2010).","journal-title":"Chemical Communications"},{"issue":"7530","key":"ref2","doi-asserted-by":"crossref","first-page":"181","DOI":"10.1038\/nature14007","type":"journal-article","article-title":"Catalytic Enantioselective Synthesis of Quaternary Carbon Stereocentres","volume":"516","author":"Quasdorf","year":"2014","unstructured":"Quasdorf, K. W.; Overman, L. E. Catalytic Enantioselective Synthesis of Quaternary Carbon Stereocentres. Nature. 516 (7530), 181-191 (2014).","journal-title":"Nature"},{"key":"ref3","type":"book","article-title":"Polyfunctional Zinc Organometallics for Organic Synthesis","volume-title":"Handbook of Functionalized Organometallics","author":"Knochel","year":"2005","unstructured":"Knochel, P.; Leuser, H.; Cong, L.-Z.; Perrone, S.; Kneisel, F. F. Polyfunctional Zinc Organometallics for Organic Synthesis. In Handbook of Functionalized Organometallics. 251-346, Wiley-VCH Verlag GmbH. Weinhem, Germany (2005)."},{"issue":"23","key":"ref4","doi-asserted-by":"crossref","first-page":"3133","DOI":"10.1055\/s-0034-1378672","type":"journal-article","article-title":"Preparation of Functionalized Lithium, Magnesium, Aluminum, Zinc, Manganese, and Indium Organometallics From Functionalized Organic Halides","volume":"46","author":"Dagousset","year":"2014","unstructured":"Dagousset, G.; Fran\u00e7ois, C.; Le\u00f3n, T.; Blanc, R.; Sansiaume-Dagousset, E.; Knochel, P. Preparation of Functionalized Lithium, Magnesium, Aluminum, Zinc, Manganese, and Indium Organometallics From Functionalized Organic Halides. Synthesis. 46 (23), 3133-3171 (2014).","journal-title":"Synthesis"},{"issue":"8","key":"ref5","doi-asserted-by":"crossref","first-page":"2489","DOI":"10.1039\/C4CS00430B","type":"journal-article","article-title":"Advances in Tandem Reactions with Organozinc Reagents","volume":"44","author":"Kim","year":"2015","unstructured":"Kim, J. H.; Ko, Y. O.; Bouffard, J.; Lee, S.-G. Advances in Tandem Reactions with Organozinc Reagents. Chemical Society Reviews. 44 (8), 2489-2507 (2015).","journal-title":"Chemical Society Reviews"},{"issue":"8","key":"ref6","doi-asserted-by":"crossref","first-page":"1101","DOI":"10.1055\/s-0035-1561198","type":"journal-article","article-title":"Polyfunctional Zinc and Magnesium Organometallics for Organic Synthesis: Some Perspectives","volume":"48","author":"Benischke","year":"2016","unstructured":"Benischke, A. D.; Ellwart, M.; Becker, M. R.; Knochel, P. Polyfunctional Zinc and Magnesium Organometallics for Organic Synthesis: Some Perspectives. Synthesis. 48 (8), 1101-1107 (2016).","journal-title":"Synthesis"},{"issue":"43","key":"ref7","doi-asserted-by":"crossref","first-page":"14988","DOI":"10.1021\/ja0553811","type":"journal-article","article-title":"Catalytic Enantioselective Alkylations of Tetrasubstituted Olefins. Synthesis of All-Carbon Quaternary Stereogenic Centers Through Cu-Catalyzed Asymmetric Conjugate Additions of Alkylzinc Reagents to Enones","volume":"127","author":"Hird","year":"2005","unstructured":"Hird, A. W.; Hoveyda, A. H. Catalytic Enantioselective Alkylations of Tetrasubstituted Olefins. Synthesis of All-Carbon Quaternary Stereogenic Centers Through Cu-Catalyzed Asymmetric Conjugate Additions of Alkylzinc Reagents to Enones. Journal of the American Chemical Society. 127 (43), 14988-14989 (2005).","journal-title":"Journal of the American Chemical Society"},{"issue":"22","key":"ref8","doi-asserted-by":"crossref","first-page":"7182","DOI":"10.1021\/ja062061o","type":"journal-article","article-title":"A Practical Method for Enantioselective Synthesis of All-Carbon Quaternary Stereogenic Centers Through NHC-Cu-Catalyzed Conjugate Additions of Alkyl- and Arylzinc Reagents to \u03b2-Substituted Cyclic Enones","volume":"128","author":"Lee","year":"2006","unstructured":"Lee, K.-S.; Brown, M. K.; Hird, A. W.; Hoveyda, A. H. A Practical Method for Enantioselective Synthesis of All-Carbon Quaternary Stereogenic Centers Through NHC-Cu-Catalyzed Conjugate Additions of Alkyl- and Arylzinc Reagents to \u03b2-Substituted Cyclic Enones. Journal of the American Chemical Society. 128 (22), 7182-7184 (2006).","journal-title":"Journal of the American Chemical Society"},{"issue":"7","key":"ref9","doi-asserted-by":"crossref","first-page":"1097","DOI":"10.1002\/anie.200604511","type":"journal-article","article-title":"All-Carbon Quaternary Stereogenic Centers by Enantioselective Cu-Catalyzed Conjugate Additions Promoted by a Chiral N-Heterocyclic Carbene","volume":"46","author":"Brown","year":"2007","unstructured":"Brown, M. K.; May, T. L.; Baxter, C. A.; Hoveyda, A. H. All-Carbon Quaternary Stereogenic Centers by Enantioselective Cu-Catalyzed Conjugate Additions Promoted by a Chiral N-Heterocyclic Carbene. Angewandte Chemie International Edition. 46 (7), 1097-1100 (2007).","journal-title":"Angewandte Chemie International Edition"},{"issue":"10","key":"ref10","doi-asserted-by":"crossref","first-page":"2390","DOI":"10.1021\/jo00245a057","type":"journal-article","article-title":"Synthesis and Reactivity Toward Acyl Chlorides and Enones of the New Highly Functionalized Copper Reagents RCu(CN)ZnI","volume":"53","author":"Knochel","year":"1998","unstructured":"Knochel, P.; Yeh, M. C. P.; Berk, S. C.; Talbert, J. Synthesis and Reactivity Toward Acyl Chlorides and Enones of the New Highly Functionalized Copper Reagents RCu(CN)ZnI.The Journal of Organic Chemistry. 53 (10), 2390-2392 (1998).","journal-title":"The Journal of Organic Chemistry"},{"issue":"51","key":"ref11","doi-asserted-by":"crossref","first-page":"6693","DOI":"10.1016\/S0040-4039(00)82430-2","type":"journal-article","article-title":"1,4-Additions of the Highly Functionalized Copper Reagents RCu(CN)-ZnI\u20222 BF3 to Trisubstituted Enones. A New BF3 Promoted Cyclization Reaction","volume":"29","author":"Yeh","year":"1988","unstructured":"Yeh, M. C. P.; Knochel, P.; Butler, W. M.; Berk, S. C. 1,4-Additions of the Highly Functionalized Copper Reagents RCu(CN)-ZnI\u20222 BF3 to Trisubstituted Enones. A New BF3 Promoted Cyclization Reaction. Tetrahedron Letters. 29 (51), 6693-6696 (1988).","journal-title":"Tetrahedron Letters"},{"issue":"22","key":"ref12","doi-asserted-by":"crossref","first-page":"5202","DOI":"10.1021\/jo00283a006","type":"journal-article","article-title":"Nucleophilic Reactivity of Zinc and Copper Carbenoids. Part II","volume":"54","author":"Knochel","year":"1989","unstructured":"Knochel, P.; Chou, T. S.; Chen, H. G.; Yeh, M. C. P.; Rozema, M. J. Nucleophilic Reactivity of Zinc and Copper Carbenoids. Part II. The Journal of Organic Chemistry. 54 (22), 5202-5204 (1989).","journal-title":"The Journal of Organic Chemistry"},{"issue":"3","key":"ref13","doi-asserted-by":"crossref","first-page":"351","DOI":"10.1002\/anie.198903511","type":"journal-article","article-title":"Copper(I)-Promoted Michael-Addition Reaction of Organozincs of Esters, Nitriles, and \u03b1-Amino Acids","volume":"28","author":"Tamaru","year":"1989","unstructured":"Tamaru, Y.; Tanigawa, H.; Yamamoto, T.; Yoshida, Z. I. Copper(I)-Promoted Michael-Addition Reaction of Organozincs of Esters, Nitriles, and \u03b1-Amino Acids. Angewandte Chemie International Edition. 28 (3), 351-353 (1989).","journal-title":"Angewandte Chemie International Edition"},{"issue":"23","key":"ref14","doi-asserted-by":"crossref","first-page":"14723","DOI":"10.1021\/acs.joc.8b02201","type":"journal-article","article-title":"Access to Functionalized Quaternary Stereocenters via the Copper-Catalyzed Conjugate Addition of Monoorganozinc Bromide Reagents Enabled by N,N-Dimethylacetamide","volume":"83","author":"Fulton","year":"2018","unstructured":"Fulton, T. J.; Alley, P. L.; Rensch, H. R.; Ackerman, A. M.; Berlin, C. B.; Krout, M. R. Access to Functionalized Quaternary Stereocenters via the Copper-Catalyzed Conjugate Addition of Monoorganozinc Bromide Reagents Enabled by N,N-Dimethylacetamide. The Journal of Organic Chemistry. 83 (23), 14723-14732 (2018).","journal-title":"The Journal of Organic Chemistry"},{"issue":"36","key":"ref15","doi-asserted-by":"crossref","first-page":"6040","DOI":"10.1002\/anie.200601450","type":"journal-article","article-title":"Efficient Synthesis of Functionalized Organozinc Compounds by the Direct Insertion of Zinc into Organic Iodides and Bromides","volume":"45","author":"Krasovskiy","year":"2006","unstructured":"Krasovskiy, A.; Malakhov, V.; Gavryushin, A.; Knochel, P. Efficient Synthesis of Functionalized Organozinc Compounds by the Direct Insertion of Zinc into Organic Iodides and Bromides. Angewandte Chemie International Edition. 45 (36), 6040-6044 (2006).","journal-title":"Angewandte Chemie International Edition"},{"issue":"4","key":"ref16","doi-asserted-by":"crossref","first-page":"423","DOI":"10.1021\/ol0272693","type":"journal-article","article-title":"Highly Efficient, General Procedure for the Preparation of Alkylzinc Reagents from Unactivated Alkyl Bromides and Chlorides","volume":"5","author":"Huo","year":"2003","unstructured":"Huo, S. Highly Efficient, General Procedure for the Preparation of Alkylzinc Reagents from Unactivated Alkyl Bromides and Chlorides. Organic Letters. 5 (4), 423-425 (2003).","journal-title":"Organic Letters"},{"issue":"14","key":"ref17","doi-asserted-by":"crossref","first-page":"2923","DOI":"10.1021\/jo00408a041","type":"journal-article","article-title":"Rapid Chromatographic Technique for Preparative Separations with Moderate Resolution","volume":"43","author":"Still","year":"1978","unstructured":"Still, W. C.; Kahn, M.; Mitra, A. Rapid Chromatographic Technique for Preparative Separations with Moderate Resolution. The Journal of Organic Chemistry. 43 (14), 2923-2925 (1978).","journal-title":"The Journal of Organic Chemistry"},{"issue":"22","key":"ref18","doi-asserted-by":"crossref","first-page":"3835","DOI":"10.1021\/ol026644o","type":"journal-article","article-title":"Tandem Asymmetric Conjugate Addition-Silylation of Enantiomerically Enriched Zinc Enolates. Synthetic Importance and Mechanistic Implications","volume":"4","author":"Knopff","year":"2002","unstructured":"Knopff, O.; Alexakis, A. Tandem Asymmetric Conjugate Addition-Silylation of Enantiomerically Enriched Zinc Enolates. Synthetic Importance and Mechanistic Implications. Organic Letters. 4 (22), 3835-3837 (2002).","journal-title":"Organic Letters"}],"container-title":["Journal of Visualized Experiments"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.jove.com\/t\/59775\/efficient-synthesis-all-carbon-quaternary-centers-via-conjugate","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,10,22]],"date-time":"2026-10-22T00:57:36Z","timestamp":1792630656000},"score":1,"resource":{"primary":{"URL":"https:\/\/app.jove.com\/t\/59775"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2019,5,26]]},"references-count":18,"journal-issue":{"issue":"147","published-online":{"date-parts":[[2019]]}},"URL":"https:\/\/doi.org\/10.3791\/59775","relation":{},"ISSN":["1940-087X"],"issn-type":[{"value":"1940-087X","type":"electronic"}],"subject":[],"published":{"date-parts":[[2019,5,26]]}}}