@article{c4d7f6975a6044db9b902990cb95e206,
title = "Conformationally Biased Ketones React Diastereoselectively with Allylmagnesium Halides",
abstract = "The addition of the highly reactive reagent allylmagnesium halide to α-substituted acyclic chiral ketones proceeded with high stereoselectivity. The stereoselectivity cannot be analyzed by conventional stereochemical models because these reactions do not conform to the requirements of those models. Instead, the stereoselectivity arises from the approach of the nucleophile to the most accessible diastereofaces of the lowest-energy conformations of the ketones. High stereoselectivity is expected, and the stereochemical outcome can be predicted, with conformationally biased ketones that have sterically distinguishable diastereofaces wherein only one face is accessible for nucleophilic addition. The conformations of the ketones can be determined by a combination of computational modeling and, in some cases, structure determination by X-ray crystallography.",
author = "Bartolo, {Nicole D.} and Demkiw, {Krystyna M.} and Read, {Jacquelyne A.} and Valent{\'i}n, {Elizabeth M.} and Yingying Yang and Dillon, {Alexandra M.} and Hu, {Chunhua T.} and Ward, {Michael D.} and Woerpel, {K. A.}",
note = "Funding Information: This research was supported by the National Institutes of Health, National Institute of General Medical Sciences (1R01GM129286). K.M.D. acknowledges the NYU Department of Chemistry for support in the form of a Margaret Strauss Kramer Fellowship. A.M.D. and M.D.W. acknowledge support provided by the National Science Foundation, Divisions of Materials Research (DMR-2002964). We acknowledge NYU{\textquoteright}s Shared Instrumentation Facility and the support provided from NSF award CHE-01162222 and NIH award S10-OD016343. We thank Dr. Chin Lin (NYU) for his help with NMR data. The X-ray facility at NYU was supported partially by the National Science Foundation (NSF) Chemistry Research Instrumentation and Facilities Program (CHE-0840277) and the Materials Research Science and Engineering Center (MRSEC) Program (DMR-1420073). Publisher Copyright: {\textcopyright} 2022 American Chemical Society. All rights reserved.",
year = "2022",
month = mar,
day = "4",
doi = "10.1021/acs.joc.1c02844",
language = "English (US)",
volume = "87",
pages = "3042--3065",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "5",
}