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One-pot highly enantioselective catalytic Mannich-type reactions between aldehydes and stable α-amido sulfones: asymmetric synthesis of β-amino aldehydes and β-amino acids

One-pot highly enantioselective catalytic Mannich-type reactions between aldehydes and stable α-amido sulfones: asymmetric synthesis of β-amino aldehydes and β-amino acids
One-pot highly enantioselective catalytic Mannich-type reactions between aldehydes and stable α-amido sulfones: asymmetric synthesis of β-amino aldehydes and β-amino acids
A highly enantioselective catalytic route to carbamate- and benzoate-protected β-amino aldehydes and β-amino acids is presented. The amino acid-catalyzed one-pot asymmetric reaction between unmodified aldehydes and α-amido sulfones gives the corresponding β-amino compounds with up to 95:5 dr and 97–>99% ee.
0040-4039
234-237
Deiana, Luca
3eff57b4-a9f5-4c7f-a484-4dee1588e5de
Zhao, Gui-Ling
106737c0-2aeb-4805-a8d7-496b1ce04322
Dziedzic, Pawel
f1a3d742-6349-4e42-82c5-98f005aab0f7
Rios, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441
Vesely, Jan
1853ff19-a906-4321-bd69-f7e434176fc3
Ekström, Jesper
e4fd1547-38dc-426f-bfce-aaf3d96e67db
Córdova, Armando
d2a1239f-708d-4f9c-bf7c-c095e9a27cac
Deiana, Luca
3eff57b4-a9f5-4c7f-a484-4dee1588e5de
Zhao, Gui-Ling
106737c0-2aeb-4805-a8d7-496b1ce04322
Dziedzic, Pawel
f1a3d742-6349-4e42-82c5-98f005aab0f7
Rios, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441
Vesely, Jan
1853ff19-a906-4321-bd69-f7e434176fc3
Ekström, Jesper
e4fd1547-38dc-426f-bfce-aaf3d96e67db
Córdova, Armando
d2a1239f-708d-4f9c-bf7c-c095e9a27cac

Deiana, Luca, Zhao, Gui-Ling, Dziedzic, Pawel, Rios, Ramon, Vesely, Jan, Ekström, Jesper and Córdova, Armando (2010) One-pot highly enantioselective catalytic Mannich-type reactions between aldehydes and stable α-amido sulfones: asymmetric synthesis of β-amino aldehydes and β-amino acids. Tetrahedron Letters, 51 (2), 234-237. (doi:10.1016/j.tetlet.2009.10.130).

Record type: Article

Abstract

A highly enantioselective catalytic route to carbamate- and benzoate-protected β-amino aldehydes and β-amino acids is presented. The amino acid-catalyzed one-pot asymmetric reaction between unmodified aldehydes and α-amido sulfones gives the corresponding β-amino compounds with up to 95:5 dr and 97–>99% ee.

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Published date: 13 January 2010
Organisations: Chemistry

Identifiers

Local EPrints ID: 347741
URI: http://eprints.soton.ac.uk/id/eprint/347741
ISSN: 0040-4039
PURE UUID: 396c8c56-3e0b-4a00-bdf2-7b12230ab0f3
ORCID for Ramon Rios: ORCID iD orcid.org/0000-0002-3843-8521

Catalogue record

Date deposited: 29 Jan 2013 14:13
Last modified: 10 Dec 2019 01:37

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