Mid Sweden University

miun.sePublications
Change search
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf
Asymmetric Aza-Morita-Baylis-Hillman-type reactions: The highly enantioselective reaction between unmodified α,β-unsaturated aldehydes and N-acyl imines by organo-co-catalysis
Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics. (armando cordova)
Charles Univ Prague, Fac Sci, Dept Organ & Nucl Chem, Prague 12840, Czech Republic .
Univ Stockholm, Arrhenius Lab, Dept Organ Chem, S-10691 Stockholm, Sweden.
Charles Univ Prague, Fac Sci, Dept Organ & Nucl Chem, Prague 12840, Czech Republic .
2011 (English)In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, ISSN 1615-4150, Vol. 353, no 7, p. 1096-1108Article in journal (Refereed) Published
Abstract [en]

The highly enantioselective organo-co-catalytic aza-Morita-Baylis-Hillman (MBH)-type reaction between N-carbamate-protected imines and alpha,beta-unsaturated aldehydes has been developed. The organic co-catalytic system of proline and 1,4-diazabicyclo[2.2.2]octane (DABCO) enables the asymmetricsynthesis of the corresponding N-Boc- and N-Cbz-protected beta-amino-alpha-alkylidene-aldehydes in good to high yields and up to 99% ee. In the case of aza-MBH-type addition of enals to phenylprop-2-ene-1-imines, the co-catalytic reaction exhibits excellent 1,2-selectivity. The organo-co-catalytic aza-MBH-type reaction can also be performed by the direct highly enantioselective addition of alpha,beta-unsaturated aldehydes to bench-stable N-carbamate-protected alpha-amidosulfones to give the corresponding beta-amino-alpha-alkylidene-aldehydes with up to 99% ee. The organo-co-catalytic aza-MBH-type reaction is also an expeditious entry to nearly enantiomerically pure beta-amino-alpha-alkylidene-amino acids and beta-amino-alpha-alkylidene-lactams (99% ee). The mechanism and stereochemistry of the chiral amine and DABCO co-catalyzed aza-MBH-type reaction are also discussed.

Place, publisher, year, edition, pages
2011. Vol. 353, no 7, p. 1096-1108
Keywords [en]
N-acylimines; amino acids; aza-Morita-Baylis-Hillman-type reaction; enantioselectivity; organo-co-catalysis; alpha, beta-unsaturated aldehydes
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:miun:diva-13898DOI: 10.1002/adsc.201000951ISI: 000290615200012Scopus ID: 2-s2.0-79955903587OAI: oai:DiVA.org:miun-13898DiVA, id: diva2:420299
Available from: 2011-05-31 Created: 2011-05-31 Last updated: 2025-09-25Bibliographically approved

Open Access in DiVA

No full text in DiVA

Other links

Publisher's full textScopus

Authority records

Cordova, Armando

Search in DiVA

By author/editor
Cordova, Armando
By organisation
Department of Natural Sciences, Engineering and Mathematics
In the same journal
Advanced Synthesis and Catalysis
Organic Chemistry

Search outside of DiVA

GoogleGoogle Scholar

doi
urn-nbn

Altmetric score

doi
urn-nbn
Total: 1256 hits
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf