In this section
@article{Braddock:2023:10.1021/acs.joc.3c00672,
author = {Braddock, D and Lancaster, B and Tighe, C and White, A},
doi = {10.1021/acs.joc.3c00672},
journal = {Journal of Organic Chemistry},
pages = {8904--8914},
title = {Surmounting byproduct inhibition in an intermolecular catalytic asymmetric alkene bromoesterification reaction as revealed by kinetic profiling},
url = {http://dx.doi.org/10.1021/acs.joc.3c00672},
volume = {88},
year = {2023}
}
TY - JOUR
AB - Kinetic profiling has shown that a (DHQD)2PHAL catalysed intermolecular asymmetric alkene bromoesterification reaction is inhibited by primary amides, imides, hydantoins and secondary cyclic amides, which are by-products of common stoichiometric bromenium ion sources. Two approaches to resolving the inhibition are presented enabling the (DHQD)2PHAL loading to be dropped from 10 to 1 mol% while maintaining high bromoester conversions over short reaction times. Iterative post-reaction recrystallisations enabled a homochiral bromonaphthoate ester to be synthesised using only 1 mol% (DHQD)2PHAL.
AU - Braddock,D
AU - Lancaster,B
AU - Tighe,C
AU - White,A
DO - 10.1021/acs.joc.3c00672
EP - 8914
PY - 2023///
SN - 0022-3263
SP - 8904
TI - Surmounting byproduct inhibition in an intermolecular catalytic asymmetric alkene bromoesterification reaction as revealed by kinetic profiling
T2 - Journal of Organic Chemistry
UR - http://dx.doi.org/10.1021/acs.joc.3c00672
UR - https://pubs.acs.org/doi/10.1021/acs.joc.3c00672
UR - http://hdl.handle.net/10044/1/104746
VL - 88
ER -