Published April 14, 2010 | Version Accepted Version + Supplemental Material
Journal Article Open

Enantioselective Alkenylation via Nickel-Catalyzed Cross-Coupling with Organozirconium Reagents

  • 1. ROR icon Massachusetts Institute of Technology

Abstract

A new family of organometallic compounds, organozirconium reagents, are shown to serve as suitable partners in cross-coupling reactions of (activated) secondary alkyl electrophiles. Thus, the first catalytic method for coupling secondary α-bromoketones with alkenylmetal reagents has been developed, specifically, a mild, versatile, and stereoconvergent carbon−carbon bond-forming process that generates potentially labile β,γ-unsaturated ketones with good enantioselectivity.

Additional Information

© 2010 American Chemical Society. Received February 28, 2010. Support has been provided by the National Institutes of Health (National Institute of General Medical Sciences, Grant R01-GM62871), Merck Research Laboratories, and Novartis. We thank Shaun D. Fontaine, Dr. Peter Mueller, and Dr. Michael R. Reithofer for assistance.

Attached Files

Accepted Version - nihms189896.pdf

Supplemental Material - ja1017046_si_001.cif

Supplemental Material - ja1017046_si_002.pdf

Files

ja1017046_si_002.pdf

Files (2.9 MB)

Name Size
md5:30c71ccf520e02c57a620667aaf1268c
28.4 kB Download
md5:9094a112bebe5cff43cab2a8913d9ace
2.5 MB Preview Download
md5:71b445a0ab65364eaca15aeaefd60642
406.1 kB Preview Download

Additional details

Identifiers

PMCID
PMC2860276
Eprint ID
102860
DOI
10.1021/ja1017046
Resolver ID
CaltechAUTHORS:20200428-095146456

Related works

Describes
10.1021/ja1017046 (DOI)

Funding

NIH
R01-GM62871
Merck Research Laboratories
Novartis

Dates

Created
2020-04-29
Created from EPrint's datestamp field
Updated
2021-11-16
Created from EPrint's last_modified field