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The generation of difluoroenolates from trifluoroethanol and reproducible syntheses of ?,?-difluoro-?-hydroxy ketones

The generation of difluoroenolates from trifluoroethanol and reproducible syntheses of ?,?-difluoro-?-hydroxy ketones
The generation of difluoroenolates from trifluoroethanol and reproducible syntheses of ?,?-difluoro-?-hydroxy ketones
Metallated difluoroenol carbamate 1 reacted with aldehydes and ketones in the presence of highly oxophilic Lewis acid boron trifluoride-ethyl ether; the Lewis acid attenuated the transacylation reaction to the corresponding enolates so that allylic alcohols could be isolated. Treatment of the allylic alcohols with strong base afforded difluoroenolates which could be trapped cleanly in aldol reactions.
organofluorine-organosilicon chemistry, containing building-blocks, heart chymase inhibitors, enol silyl ethers, chlorodifluoromethyl ketones, convenient synthesis, hiv-1 protease, trifluoromethyltrimethylsilane, acylsilanes, derivatives
2525-2535
Balnaves, A.S.
b96404d3-e575-44b6-bfcb-c2df7e81e9b1
Gelbrich, T.
6874d813-bf11-4950-b322-dfe77c533f41
Hursthouse, M.B.
427032bc-428c-4396-adb0-b38e87e908e7
Light, M.E.
d04ad463-ba94-4c59-ab35-a64901f32501
Palmer, M.J.
6131bd7e-29b2-4e87-86ca-de7ab2377a94
Percy, J.M.
22b15260-f74f-4b3b-ab8e-d2b65488c08f
Balnaves, A.S.
b96404d3-e575-44b6-bfcb-c2df7e81e9b1
Gelbrich, T.
6874d813-bf11-4950-b322-dfe77c533f41
Hursthouse, M.B.
427032bc-428c-4396-adb0-b38e87e908e7
Light, M.E.
d04ad463-ba94-4c59-ab35-a64901f32501
Palmer, M.J.
6131bd7e-29b2-4e87-86ca-de7ab2377a94
Percy, J.M.
22b15260-f74f-4b3b-ab8e-d2b65488c08f

Balnaves, A.S., Gelbrich, T., Hursthouse, M.B., Light, M.E., Palmer, M.J. and Percy, J.M. (1999) The generation of difluoroenolates from trifluoroethanol and reproducible syntheses of ?,?-difluoro-?-hydroxy ketones. Journal of the Chemical Society, Perkin Transactions 1, (17), 2525-2535.

Record type: Article

Abstract

Metallated difluoroenol carbamate 1 reacted with aldehydes and ketones in the presence of highly oxophilic Lewis acid boron trifluoride-ethyl ether; the Lewis acid attenuated the transacylation reaction to the corresponding enolates so that allylic alcohols could be isolated. Treatment of the allylic alcohols with strong base afforded difluoroenolates which could be trapped cleanly in aldol reactions.

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More information

Published date: 1999
Keywords: organofluorine-organosilicon chemistry, containing building-blocks, heart chymase inhibitors, enol silyl ethers, chlorodifluoromethyl ketones, convenient synthesis, hiv-1 protease, trifluoromethyltrimethylsilane, acylsilanes, derivatives

Identifiers

Local EPrints ID: 39134
URI: http://eprints.soton.ac.uk/id/eprint/39134
PURE UUID: 94e988b5-3f79-48c1-8418-55864d77a385

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Date deposited: 18 Jul 2006
Last modified: 23 Jul 2020 16:42

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