Fulton, Tyler J. and Alley, Phebe L. and Rensch, Heather R. and Ackerman, Adriana M. and Berlin, Cameron B. and Krout, Michael R. (2018) Access to Functionalized Quaternary Stereocenters via the Copper-Catalyzed Conjugate Addition of Monoorganozinc Bromide Reagents Enabled by N,N-Dimethylacetamide. Journal of Organic Chemistry, 83 (23). pp. 14723-14732. ISSN 0022-3263. doi:10.1021/acs.joc.8b02201. https://resolver.caltech.edu/CaltechAUTHORS:20181030-154210846
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Abstract
Monoorganozinc reagents, readily obtained from alkyl bromides, display excellent reactivity with β,β-disubstituted enones and TMSCl in the presence of Cu(I) and Cu(II) salts to synthesize a variety of cyclic functionalized β-quaternary ketones in 38–99% yields and 9:1–20:1 diastereoselectivities. The conjugate addition features a pronounced improvement in DMA using monoorganozinc bromide reagents. A simple one-pot protocol that harnesses in situ generated monoorganozinc reagents delivers comparable product yields.
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| Additional Information: | © 2018 American Chemical Society. Received: August 25, 2018; Published: October 30, 2018. The authors thank the American Chemical Society (ACS) Petroleum Research Fund Undergraduate New Investigator Program (Award No. 58488-UNI1), the ACS and Pfizer (research fellowship to T.J.F.), Bucknell University (research fellowships to H.R.R. and T.J.F.), and the Department of Chemistry (research fellowships to P.L.A, A.M.A., and C.B.B.) for generous support of this work. Dr. Peter M. Findeis and Brian Breczinski are acknowledged for experimental and instrumentation assistance. The authors declare no competing financial interest. | |||||||||
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| Issue or Number: | 23 | |||||||||
| DOI: | 10.1021/acs.joc.8b02201 | |||||||||
| Record Number: | CaltechAUTHORS:20181030-154210846 | |||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20181030-154210846 | |||||||||
| Official Citation: | Access to Functionalized Quaternary Stereocenters via the Copper-Catalyzed Conjugate Addition of Monoorganozinc Bromide Reagents Enabled by N,N-Dimethylacetamide. Tyler J. Fulton, Phebe L. Alley, Heather R. Rensch, Adriana M. Ackerman, Cameron B. Berlin, and Michael R. Krout. The Journal of Organic Chemistry 2018 83 (23), 14723-14732 DOI: 10.1021/acs.joc.8b02201 | |||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | |||||||||
| ID Code: | 90528 | |||||||||
| Collection: | CaltechAUTHORS | |||||||||
| Deposited By: | Tony Diaz | |||||||||
| Deposited On: | 30 Oct 2018 22:57 | |||||||||
| Last Modified: | 16 Nov 2021 03:33 |
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