@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}
}

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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  - 

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