Studying the reactivity of alkyl substituted BODIPYs: first enantioselective addition of BODIPY to MBH carbonates
Studying the reactivity of alkyl substituted BODIPYs: first enantioselective addition of BODIPY to MBH carbonates
The first enantioselective addition of alkyl BODIPYs to Morita-Baylis-Hillman (MBH) carbonates is reported. This is the first reported enantioselective methodology using the methylene position of BODIPYs as a nucleophile. The reaction is efficiently catalyzed by cinchona alkaloids, achieving high enantioselectivities and total diastereoselectivity. The use of cinchona alkaloid pseudo enantiomers (chinine/cinchonine) allows us to obtain both pairs of enantiomers in similar yields and enantioselectivities, a common issue in this type of reaction. The photophysical study of these dyes (absorption and fluorescence) has been performed in order to determine their parameters and explore future possible application in bioimaging. In addition, electronic circular dichroism (ECD) studies supported by time-dependent density functional theory (TD-DFT) calculations were also performed.
4503-4508
Meazza, Marta
c4665645-8c77-4cfd-aa02-6bcc3341c1aa
Cruz, Carlos M.
800e6e57-e269-4d19-ad6b-3b449df8130a
Ortuño, Ana M.
44c77cfb-7ece-472e-82b2-c818ca173fe0
Cuerva, Juan M.
56d42f49-00bb-44c1-b1f5-2fcdf240c272
Crovetto, Luis
45d4cd97-3fe5-4498-a861-bc06492eb09d
Rios, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441
28 March 2021
Meazza, Marta
c4665645-8c77-4cfd-aa02-6bcc3341c1aa
Cruz, Carlos M.
800e6e57-e269-4d19-ad6b-3b449df8130a
Ortuño, Ana M.
44c77cfb-7ece-472e-82b2-c818ca173fe0
Cuerva, Juan M.
56d42f49-00bb-44c1-b1f5-2fcdf240c272
Crovetto, Luis
45d4cd97-3fe5-4498-a861-bc06492eb09d
Rios, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441
Meazza, Marta, Cruz, Carlos M., Ortuño, Ana M., Cuerva, Juan M., Crovetto, Luis and Rios, Ramon
(2021)
Studying the reactivity of alkyl substituted BODIPYs: first enantioselective addition of BODIPY to MBH carbonates.
Chemical Science, 12 (12), .
(doi:10.1039/D0SC06574A).
Abstract
The first enantioselective addition of alkyl BODIPYs to Morita-Baylis-Hillman (MBH) carbonates is reported. This is the first reported enantioselective methodology using the methylene position of BODIPYs as a nucleophile. The reaction is efficiently catalyzed by cinchona alkaloids, achieving high enantioselectivities and total diastereoselectivity. The use of cinchona alkaloid pseudo enantiomers (chinine/cinchonine) allows us to obtain both pairs of enantiomers in similar yields and enantioselectivities, a common issue in this type of reaction. The photophysical study of these dyes (absorption and fluorescence) has been performed in order to determine their parameters and explore future possible application in bioimaging. In addition, electronic circular dichroism (ECD) studies supported by time-dependent density functional theory (TD-DFT) calculations were also performed.
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D0SC06574A
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Accepted/In Press date: 3 February 2021
e-pub ahead of print date: 5 February 2021
Published date: 28 March 2021
Identifiers
Local EPrints ID: 447003
URI: http://eprints.soton.ac.uk/id/eprint/447003
ISSN: 1478-6524
PURE UUID: e1fa596b-df3f-4e28-832d-5a9b5c8c4490
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Date deposited: 01 Mar 2021 17:34
Last modified: 16 Mar 2024 10:58
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Contributors
Author:
Marta Meazza
Author:
Carlos M. Cruz
Author:
Ana M. Ortuño
Author:
Juan M. Cuerva
Author:
Luis Crovetto
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