Surmounting By-Product Inhibition in an Intermolecular Catalytic Asymmetric Alkene Bromoesterification Reaction as Revealed by Kinetic Profiling
DOI: 10.14469/hpc/12349 Metadata
Created: 2023-03-07 11:49
Last modified: 2023-03-29 08:27
License: Creative Commons: Public Domain Dedication 1.0
Funding: (none given)
Co-author: Ben Lancaster Co-author: Christopher J Tighe Co-author: D. Christopher Braddock
Description
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. Furthermore, iterative post-reaction recrystallisations enabled a homochiral bromonaphthoate ester to be synthesised using only 1 mol% (DHQD)2PHAL.
Members
| DOI | Description |
|---|---|
| 10.14469/hpc/12352 | PhCONHBr (3) |
| 10.14469/hpc/12355 | (+)-(1S,2S)-2-Bromo-1,2,3,4-tetrahydronaphthalen-1-yl benzoate (5) |
| 10.14469/hpc/12356 | PhCONBr(t-Bu) (9) |
| 10.14469/hpc/12357 | PhCONBrMe (10) |
| 10.14469/hpc/12358 | (+)-(1S,2S)-2-Bromo-1,2,3,4-tetrahydronaphthalen-1-yl 1-naphthoate (13) |
| 10.14469/hpc/12359 | (−)-(1S,2S)-2-Bromo-1,2,3,4-tetrahydronaphthalen-1-ol (15) |
| 10.14469/hpc/12420 | 4•(Saccharin)2 (8) |