Published December 7, 2018
| Version Supplemental Material
Journal Article
Open
Access to Functionalized Quaternary Stereocenters via the Copper-Catalyzed Conjugate Addition of Monoorganozinc Bromide Reagents Enabled by N,N-Dimethylacetamide
Creators
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1.
California Institute of Technology
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2.
Bucknell University
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.
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.Attached Files
Supplemental Material - jo8b02201_si_001.pdf
Files
jo8b02201_si_001.pdf
Additional details
Identifiers
- Eprint ID
- 90528
- DOI
- 10.1021/acs.joc.8b02201
- Resolver ID
- CaltechAUTHORS:20181030-154210846
Related works
- Describes
- 10.1021/acs.joc.8b02201 (DOI)
Funding
- American Chemical Society Petroleum Research Fund
- 58488-UNI1
- Pfizer
- Bucknell University
Dates
- Created
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2018-10-30Created from EPrint's datestamp field
- Updated
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2021-11-16Created from EPrint's last_modified field