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Literature DB >> 18834197

Chiral tetraaminophosphonium carboxylate-catalyzed direct Mannich-type reaction.

Daisuke Uraguchi¹, Yusuke Ueki, Takashi Ooi.

Abstract

The cooperative asymmetric catalysis of chiral tetraaminophosphonium carboxylate (P,S)-1.OCOR has been established, and its synthetic utility has been successfully demonstrated by application to the highly enantioselective direct Mannich-type reaction of azlactones with N-sulfonyl imines. The present study stimulates the cultivation of the potential of the chiral quaternary onium salt catalysis by the structural modification of organic anion.

Entities: Chemical

Year: 2008 PMID： 18834197 DOI： 10.1021/ja806311e

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

7 in total

1. Base-catalyzed direct aldolization of α-alkyl-α-hydroxy trialkyl phosphonoacetates.

Authors: Michael T Corbett; Daisuke Uraguchi; Takashi Ooi; Jeffrey S Johnson
Journal: Angew Chem Int Ed Engl Date: 2012-04-04 Impact factor: 15.336

2. Gold(I)-catalyzed diastereo- and enantioselective 1,3-dipolar cycloaddition and Mannich reactions of azlactones.

Authors: Asa D Melhado; Giovanni W Amarante; Z Jane Wang; Marco Luparia; F Dean Toste
Journal: J Am Chem Soc Date: 2011-02-22 Impact factor: 15.419

3. Cyclopropenimine-catalyzed enantioselective Mannich reactions of tert-butyl glycinates with N-Boc-imines.

Authors: Jeffrey S Bandar; Tristan H Lambert
Journal: J Am Chem Soc Date: 2013-08-01 Impact factor: 15.419

Review 4. Asymmetric ion-pairing catalysis.

Authors: Katrien Brak; Eric N Jacobsen
Journal: Angew Chem Int Ed Engl Date: 2012-11-28 Impact factor: 15.336

Chiral tetraaminophosphonium carboxylate-catalyzed direct Mannich-type reaction.

1. Base-catalyzed direct aldolization of α-alkyl-α-hydroxy trialkyl phosphonoacetates.

2. Gold(I)-catalyzed diastereo- and enantioselective 1,3-dipolar cycloaddition and Mannich reactions of azlactones.

3. Cyclopropenimine-catalyzed enantioselective Mannich reactions of tert-butyl glycinates with N-Boc-imines.

Review 4. Asymmetric ion-pairing catalysis.

5. Enantioselective cycloaddition of münchnones onto [60]fullerene: organocatalysis versus metal catalysis.

6. Phosphazene-catalyzed desymmetrization of cyclohexadienones by dithiane addition.

7. Carboxylate Catalyzed Isomerization of β,γ-Unsaturated N-Acetylcysteamine Thioesters.