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Highly stereoselective synthesis of spiropyrazolones

Highly stereoselective synthesis of spiropyrazolones
Highly stereoselective synthesis of spiropyrazolones
The synthesis of spiro compounds through a Michael-Michael-aldol reaction is reported. The reaction affords spiropyrazolone derivatives in good yields, in almost diastereo- and enantiopure form, and is catalyzed by diphenylprolinol derivatives. The reaction showed strong nonlinear effects. Remarkably, when a catalyst with 70% ee is used, the reaction still affords the final spiro compound in almost diastereo- and enantiopure form.
diastereoselectivity, enantioselectivity, michael addition, organocatalysis, spiro compounds
1434-193X
1318-1325
Alba, Andrea-Nekane R.
d1750aca-a087-449c-8466-11fb54264bea
Zea, Alex
e1cc8e2a-e3f2-46a2-8463-3015712bdb96
Valero, Guillem
c5f692fe-3b07-4916-a4ec-23f78a45cc15
Calbet, Teresa
f09dc31e-22d8-4f56-9a48-6b71cdcccd27
Font-Bardía, Merce
3e683e82-33e4-4cf9-8a20-668a10dd620e
Mazzanti, Andrea
1e31a7a1-e163-4bd4-9e72-42bc64f60277
Moyano, Albert
07f92405-40f4-4fc4-97b3-9bd5c9c14baa
Rios, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441
Alba, Andrea-Nekane R.
d1750aca-a087-449c-8466-11fb54264bea
Zea, Alex
e1cc8e2a-e3f2-46a2-8463-3015712bdb96
Valero, Guillem
c5f692fe-3b07-4916-a4ec-23f78a45cc15
Calbet, Teresa
f09dc31e-22d8-4f56-9a48-6b71cdcccd27
Font-Bardía, Merce
3e683e82-33e4-4cf9-8a20-668a10dd620e
Mazzanti, Andrea
1e31a7a1-e163-4bd4-9e72-42bc64f60277
Moyano, Albert
07f92405-40f4-4fc4-97b3-9bd5c9c14baa
Rios, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441

Alba, Andrea-Nekane R., Zea, Alex, Valero, Guillem, Calbet, Teresa, Font-Bardía, Merce, Mazzanti, Andrea, Moyano, Albert and Rios, Ramon (2011) Highly stereoselective synthesis of spiropyrazolones. European Journal of Organic Chemistry, 2011 (7), 1318-1325.

Record type: Article

Abstract

The synthesis of spiro compounds through a Michael-Michael-aldol reaction is reported. The reaction affords spiropyrazolone derivatives in good yields, in almost diastereo- and enantiopure form, and is catalyzed by diphenylprolinol derivatives. The reaction showed strong nonlinear effects. Remarkably, when a catalyst with 70% ee is used, the reaction still affords the final spiro compound in almost diastereo- and enantiopure form.

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More information

e-pub ahead of print date: 26 January 2011
Published date: March 2011
Keywords: diastereoselectivity, enantioselectivity, michael addition, organocatalysis, spiro compounds
Organisations: Chemistry

Identifiers

Local EPrints ID: 344070
URI: https://eprints.soton.ac.uk/id/eprint/344070
ISSN: 1434-193X
PURE UUID: bda37705-f4ff-4873-9c67-251cfbbf9507
ORCID for Ramon Rios: ORCID iD orcid.org/0000-0002-3843-8521

Catalogue record

Date deposited: 07 Jul 2016 14:09
Last modified: 06 Jun 2018 12:29

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Contributors

Author: Andrea-Nekane R. Alba
Author: Alex Zea
Author: Guillem Valero
Author: Teresa Calbet
Author: Merce Font-Bardía
Author: Andrea Mazzanti
Author: Albert Moyano
Author: Ramon Rios ORCID iD

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