@article{1111e353677b4508b438e95dff9f752a,
title = "Mechanistic Insight into Additions of Allylic Grignard Reagents to Carbonyl Compounds",
abstract = "Allylic Grignard reagents exhibit high reactivity and low selectivity in additions to carbonyl compounds. Additions of allylic Grignard reagents to carbonyl compounds were investigated using prenylmagnesium chloride as a mechanistic probe. When the carbonyl group is relatively unhindered, the addition proceeds through a six-membered transition state with allylic transposition. This process generally occurs with no diastereoselectivity because the reaction rates approach the diffusion limit. With hindered ketones, however, this pathway is disfavored, and the addition proceeds through a transition state resembling that of other Grignard reagents.",
author = "Bartolo, {Nicole D.} and Woerpel, {K. A.}",
note = "Funding Information: Acknowledgment is made to the Donors of the American Chemical Society Petroleum Research Fund for support of this research (57206-ND1). We thank Dr. Chin Lin (NYU) for assistance with NMR spectroscopy and mass spectrometry. We also thank the Molecular Design Institute of NYU for purchasing a single-crystal diffractometer and Dr. Chunhua Hu (NYU) for his assistance with data collection and structure determination. The Shared Instrumentation Facility in the Department of Chemistry was constructed through the support of the National Center for Research Resources, National Institutes of Health under Research Facilities Improvement Award Number C06 RR-16572-01. The cryogenic probe for the 600 MHz NMR was acquired through the support of the National Institute of Health S10 grant under Award Number OD016343.",
year = "2018",
month = sep,
day = "7",
doi = "10.1021/acs.joc.8b01430",
language = "English (US)",
volume = "83",
pages = "10197--10206",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "17",
}