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Asymmetric Aza-Morita–Baylis–Hillman-type reactions: The highly enantioselective reaction between unmodified α,β-unsaturated aldehydes and N-acylimines by organo-co-catal
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
2011 (English)In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 353, no 7, 1096-1108 p.Article 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 α,β-unsaturated aldehydes has been developed. The organic co-catalytic system of proline and 1,4-diazabicyclo[2.2.2]octane (DABCO) enables the asymmetric synthesis of the corresponding N-Boc- and N-Cbz-protected β-amino-α-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 α,β-unsaturated aldehydes to bench-stableN-carbamate-protected α-amidosulfones to give the corresponding β-amino-α-alkylidene-aldehydes with up to 99% ee.The organo-co-catalytic aza-MBH-type reaction is also an expeditious entry to nearly enantiomerically pure β-amino-α-alkylidene-amino acids and β-amino-α-alkylidene-lactams (99% ee). The mechanism and stereochemistry of the chiral amine and DABCO co-catalyzed aza-MBH-type reaction arealso discussed.

Place, publisher, year, edition, pages
2011. Vol. 353, no 7, 1096-1108 p.
Keyword [en]
N-acylimines, amino acids, aza-Morita–Baylis–Hillman-type reaction, enantioselectivity, organo-co-catalysis, α, β-unsaturated aldehydes
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-61617DOI: 10.1002/adsc.201000951ISI: 000290615200012OAI: oai:DiVA.org:su-61617DiVA: diva2:436575
Funder
Swedish Research Council
Available from: 2011-08-24 Created: 2011-08-24 Last updated: 2017-12-08Bibliographically approved

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