@article{b8b637bc477e4281b2edb7b01154b716,
title = "Reactions of Allylmagnesium Reagents with Carbonyl Compounds and Compounds with C═N Double Bonds: Their Diastereoselectivities Generally Cannot Be Analyzed Using the Felkin-Anh and Chelation-Control Models",
abstract = "This review describes the additions of allylmagnesium reagents to carbonyl compounds and to imines, focusing on the differences in reactivity between allylmagnesium halides and other Grignard reagents. In many cases, allylmagnesium reagents either react with low stereoselectivity when other Grignard reagents react with high selectivity, or allylmagnesium reagents react with the opposite stereoselectivity. This review collects hundreds of examples, discusses the origins of stereoselectivities or the lack of stereoselectivity, and evaluates why selectivity may not occur and when it will likely occur.",
keywords = "Alcohols/chemical synthesis, Aldehydes/chemistry, Allyl Compounds/chemistry, Ketones/chemistry, Magnesium/chemistry, Organometallic Compounds/chemistry, Stereoisomerism",
author = "Bartolo, {Nicole D.} and Read, {Jacquelyne A.} and Valent{\'i}n, {Elizabeth M.} and Woerpel, {K. A.}",
note = "Funding Information: Acknowledgment is made to the Donors of the American Chemical Society Petroleum Research Fund for partial support during the preparation of this manuscript (57206-NDI). Additional support was provided by the National Institutes of Health, National Institute of General Medical Sciences (GM-129286). K.A.W. thanks the Global Research Initiatives, NYU and NYU Florence, who graciously provided a fellowship and research facilities that allowed for time for analysis and writing of portions of the manuscript. Publisher Copyright: Copyright {\textcopyright} 2020 American Chemical Society.",
year = "2020",
month = feb,
day = "12",
doi = "10.1021/acs.chemrev.9b00414",
language = "English (US)",
volume = "120",
pages = "1513--1619",
journal = "Chemical Reviews",
issn = "0009-2665",
publisher = "American Chemical Society",
number = "3",
}