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Literature DB >> 18459795

Direct catalytic asymmetric Mannich-type reactions of gamma-butenolides: effectiveness of Brønsted acid in chiral metal catalysis.

Akitake Yamaguchi¹, Shigeki Matsunaga, Masakatsu Shibasaki.

Abstract

Direct catalytic asymmetric Mannich-type reactions of gamma-butenolides are described. A chiral Lewis acid/amine base/Brønsted acid combination was used to catalyze a gamma-addition of gamma-butenolides to N-diphenylphosphinoyl imines, affording the products in up to >99% yield, anti/syn = >97:3, and 84% ee. The use of a catalytic amount of TfOH in addition to La(OTf)3/Me-PyBox/TMEDA was important for improving yield and stereoselectivity.

Entities: Chemical Gene

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Year: 2008 PMID： 18459795 DOI： 10.1021/ol800756r

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

8 in total

1. N-Substituted tertiary and O-substituted quaternary carbon stereogenic centers by site-, diastereo- and enantioselective vinylogous Mannich reactions.

Authors: Daniel L Silverio; Peng Fu; Emma L Carswell; Marc L Snapper; Amir H Hoveyda
Journal: Tetrahedron Lett Date: 2015-04-09 Impact factor: 2.415

Review 2. Catalytic Asymmetric Synthesis of Butenolides and Butyrolactones.

Authors: Bin Mao; Martín Fañanás-Mastral; Ben L Feringa
Journal: Chem Rev Date: 2017-06-22 Impact factor: 60.622

3. Synthesis of 5,5-disubstituted butenolides based on a Pd-catalyzed gamma-arylation strategy.

Authors: Alan M Hyde; Stephen L Buchwald
Journal: Org Lett Date: 2009-06-18 Impact factor: 6.005

4. Ag-catalyzed diastereo- and enantioselective vinylogous Mannich reactions of alpha-ketoimine esters. Development of a method and investigation of its mechanism.

Authors: Laura C Wieland; Erika M Vieira; Marc L Snapper; Amir H Hoveyda
Journal: J Am Chem Soc Date: 2009-01-21 Impact factor: 15.419

5. Three-component Ag-catalyzed enantioselective vinylogous mannich and Aza-Diels-Alder reactions with alkyl-substituted aldehydes.

Authors: Hiroki Mandai; Kyoko Mandai; Marc L Snapper; Amir H Hoveyda
Journal: J Am Chem Soc Date: 2008-12-31 Impact factor: 15.419

Direct catalytic asymmetric Mannich-type reactions of gamma-butenolides: effectiveness of Brønsted acid in chiral metal catalysis.

1. N-Substituted tertiary and O-substituted quaternary carbon stereogenic centers by site-, diastereo- and enantioselective vinylogous Mannich reactions.

Review 2. Catalytic Asymmetric Synthesis of Butenolides and Butyrolactones.

3. Synthesis of 5,5-disubstituted butenolides based on a Pd-catalyzed gamma-arylation strategy.

4. Ag-catalyzed diastereo- and enantioselective vinylogous Mannich reactions of alpha-ketoimine esters. Development of a method and investigation of its mechanism.

5. Three-component Ag-catalyzed enantioselective vinylogous mannich and Aza-Diels-Alder reactions with alkyl-substituted aldehydes.

6. Direct asymmetric Michael addition to nitroalkenes: vinylogous nucleophilicity under dinuclear zinc catalysis.

7. Asymmetric catalytic synthesis of the proposed structure of trocheliophorolide B.

8. Lewis acid-catalyzed asymmetric reactions of β,γ-unsaturated 2-acyl imidazoles.