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Formal highly enantioselective organocatalytic addition of alkyl anions to alpha,beta-unsaturated aldehydes: application to the synthesis of isotope-enantiomers

Formal highly enantioselective organocatalytic addition of alkyl anions to alpha,beta-unsaturated aldehydes: application to the synthesis of isotope-enantiomers
Formal highly enantioselective organocatalytic addition of alkyl anions to alpha,beta-unsaturated aldehydes: application to the synthesis of isotope-enantiomers
For the first time, organocatalytic addition of masked alkyl chains to ?,?-unsaturated aldehydes is reported (see scheme). The addition of bisphenylsulfonylmethane takes place in high yields and with excellent enantioselectivities. Furthermore, this methodology allows the synthesis of isotope-enantiomers.
enantioselective addition, isotope effects, organocatalysis, sulfones, unsaturated aldehydes
0947-6539
11095-11099
Alba, Andrea-Nekane
e96df5c1-b984-45c5-9620-1d7f0cec8faf
Companyó, Xavier
446791db-6e0a-40f9-9f20-3a8e8af9803c
Moyano, Albert
07f92405-40f4-4fc4-97b3-9bd5c9c14baa
Rios, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441
Alba, Andrea-Nekane
e96df5c1-b984-45c5-9620-1d7f0cec8faf
Companyó, Xavier
446791db-6e0a-40f9-9f20-3a8e8af9803c
Moyano, Albert
07f92405-40f4-4fc4-97b3-9bd5c9c14baa
Rios, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441

Alba, Andrea-Nekane, Companyó, Xavier, Moyano, Albert and Rios, Ramon (2009) Formal highly enantioselective organocatalytic addition of alkyl anions to alpha,beta-unsaturated aldehydes: application to the synthesis of isotope-enantiomers. Chemistry - A European Journal, 15 (42), 11095-11099. (doi:10.1002/chem.200901806). (PMID:19780120)

Record type: Article

Abstract

For the first time, organocatalytic addition of masked alkyl chains to ?,?-unsaturated aldehydes is reported (see scheme). The addition of bisphenylsulfonylmethane takes place in high yields and with excellent enantioselectivities. Furthermore, this methodology allows the synthesis of isotope-enantiomers.

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e-pub ahead of print date: 24 September 2009
Published date: 26 October 2009
Keywords: enantioselective addition, isotope effects, organocatalysis, sulfones, unsaturated aldehydes
Organisations: Chemistry
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Identifiers

Local EPrints ID: 347730
URI: http://eprints.soton.ac.uk/id/eprint/347730
DOI: doi:10.1002/chem.200901806
ISSN: 0947-6539
PURE UUID: 22b4ab43-39f3-4684-b2f4-29b35c7cbe6b
ORCID for Ramon Rios: ORCID iD orcid.org/0000-0002-3843-8521

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Date deposited: 29 Jan 2013 13:32
Last modified: 14 Mar 2024 12:51

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Contributors

Author: Andrea-Nekane Alba
Author: Xavier Companyó
Author: Albert Moyano
Author: Ramon Rios ORCID iD

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