Synthesis of new pyrrolidine-based organocatalysts and study of their use in the asymmetric Michael addition of aldehydes to nitroolefins

Beilstein Journal of Organic Chemistry ◽

10.3762/bjoc.13.59 ◽

2017 ◽

Vol 13 ◽

pp. 612-619 ◽

Cited By ~ 1

Author(s):

Alejandro Castán ◽

Ramón Badorrey ◽

José A Gálvez ◽

María D Díaz-de-Villegas

Keyword(s):

Michael Addition ◽

Bulky Substituent ◽

Asymmetric Michael Addition ◽

Iodination Reaction ◽

Chiral Imines ◽

New Compounds ◽

The Michael Addition

New pyrrolidine-based organocatalysts with a bulky substituent at C2 were synthesized from chiral imines derived from (R)-glyceraldehyde acetonide by diastereoselective allylation followed by a sequential hydrozirconation/iodination reaction. The new compounds were found to be effective organocatalysts for the Michael addition of aldehydes to nitroolefins and enantioselectivities up to 85% ee were achieved.

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Optically Pure Aminopolyols and Polyoxamic Acid Derivatives from Aziridine-2-carboxylates

Australian Journal of Chemistry ◽

10.1071/c98026 ◽

1999 ◽

Vol 52 (4) ◽

pp. 259 ◽

Cited By ~ 10

Author(s):

Heribert Dollt ◽

Volker Zabel

Keyword(s):

Solvent Effects ◽

Michael Addition ◽

Building Blocks ◽

Bulky Substituent ◽

Cis And Trans ◽

Optically Pure ◽

The Michael Addition

Various new chiral building blocks could easily be prepared from optically pure cis and trans ethyl 3-(1′,3′- dioxolan-4′-yl)aziridine-2-carboxylates. A stereochemically pure 1,3-dioxolan in the allyl position of an α-bromoacrylate induced a high (3R*,4′S*) selectivity in the Michael addition with an amine. After oxygen at the inducing centre was exchanged with nitrogen bearing a bulky substituent, the directing influence of this new group was examined. Solvent effects influencing the cis/trans ratio of aziridine formation are discussed.

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ChemInform Abstract: The Asymmetric Michael Addition Reactions Using Chiral Imines: Application to the Synthesis of Compounds of Biological Interest

ChemInform ◽

10.1002/chin.199641281 ◽

2010 ◽

Vol 27 (41) ◽

pp. no-no

Author(s):

J. D'ANGELO ◽

C. CAVE ◽

D. DESMAELE ◽

F. DUMAS

Keyword(s):

Michael Addition ◽

Addition Reactions ◽

Asymmetric Michael Addition ◽

Biological Interest ◽

Chiral Imines

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ChemInform Abstract: Asymmetric Michael Addition of Chiral Imines to Phenylvinylsulfone: Preparation of Key Chiral Building Blocks for the Synthesis of Aspidosperma and Hunteria Alkaloids.

ChemInform ◽

10.1002/chin.199130273 ◽

2010 ◽

Vol 22 (30) ◽

pp. no-no

Author(s):

J. D'ANGELO ◽

G. REVIAL ◽

P. R. R. COSTA ◽

R. N. CASTRO ◽

O. A. C. ANTUNES

Keyword(s):

Michael Addition ◽

Building Blocks ◽

Asymmetric Michael Addition ◽

Chiral Imines

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The asymmetric michael addition process involving chiral imines : stereochemical data in support of a cyclic-like transition state

Tetrahedron Letters ◽

10.1016/0040-4039(88)85255-9 ◽

1988 ◽

Vol 29 (22) ◽

pp. 2667-2670 ◽

Cited By ~ 36

Author(s):

Jean d'Angelo ◽

André Guingant ◽

Claude Riche ◽

Angèle Chiaroni

Keyword(s):

Transition State ◽

Michael Addition ◽

Asymmetric Michael Addition ◽

Chiral Imines

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Asymmetric Michael addition of chiral imines to phenylvinylsulfone: Preparation of key chiral building blocks for the synthesis of Aspidosperma and Hunteria alkaloids.

Tetrahedron Asymmetry ◽

10.1016/s0957-4166(00)82358-7 ◽

1991 ◽

Vol 2 (3) ◽

pp. 199-202 ◽

Cited By ~ 24

Author(s):

Jean d'Angelo ◽

Gilbert Revial ◽

Paulo R.R. Costa ◽

Rosane N. Castro ◽

Octavio A.C. Antunes

Keyword(s):

Michael Addition ◽

Building Blocks ◽

Asymmetric Michael Addition ◽

Chiral Imines

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ChemInform Abstract: Enantioselective Synthesis of 2,2-Dialkyltetrahydropyran-3-ones via the Asymmetric Michael Addition Reaction Using Chiral Imines.

ChemInform ◽

10.1002/chin.199246052 ◽

2010 ◽

Vol 23 (46) ◽

pp. no-no

Author(s):

D. DESMAELE ◽

G. PAIN ◽

J. D'ANGELO

Keyword(s):

Michael Addition ◽

Addition Reaction ◽

Enantioselective Synthesis ◽

Michael Addition Reaction ◽

Asymmetric Michael Addition ◽

Chiral Imines

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Enantioselective synthesis of 2,2-dialkyltetrahydropyran-3-ones via the asymmetric Michael addition reaction using chiral imines

Tetrahedron Asymmetry ◽

10.1016/s0957-4166(00)82185-0 ◽

1992 ◽

Vol 3 (7) ◽

pp. 863-866 ◽

Cited By ~ 10

Author(s):

Didier Desmaële ◽

Gilles Pain ◽

Jean d'Angelo

Keyword(s):

Michael Addition ◽

Addition Reaction ◽

Enantioselective Synthesis ◽

Michael Addition Reaction ◽

Asymmetric Michael Addition ◽

Chiral Imines

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The asymmetric Michael addition reactions using chiral imines

Tetrahedron Asymmetry ◽

10.1016/s0957-4166(00)80251-7 ◽

1992 ◽

Vol 3 (4) ◽

pp. 459-505 ◽

Cited By ~ 248

Author(s):

Jean d'Angelo ◽

Didier Desmaële ◽

Françoise Dumas ◽

André Guingant

Keyword(s):

Michael Addition ◽

Addition Reactions ◽

Asymmetric Michael Addition ◽

Chiral Imines

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ChemInform Abstract: Stereochemical Aspects in the Asymmetric Michael Addition of Chiral Imines to Substituted Electrophilic Alkenes.

ChemInform ◽

10.1002/chin.199644039 ◽

2010 ◽

Vol 27 (44) ◽

pp. no-no

Author(s):

C. CAVE ◽

D. DESMAELE ◽

J. D'ANGELO ◽

C. RICHE ◽

A. CHIARONI

Keyword(s):

Michael Addition ◽

Asymmetric Michael Addition ◽

Chiral Imines

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ChemInform Abstract: Enantioselective Access to Five- and Six-Membered Nitrogen-Containing Heterocycles, Based on the Asymmetric Michael Addition of Chiral Imines and Chiral Enamino Esters.

ChemInform ◽

10.1002/chin.199829127 ◽

2010 ◽

Vol 29 (29) ◽

pp. no-no

Author(s):

J. D'ANGELO ◽

C. CAVE ◽

D. DESMAELE ◽

A. GASSAMA ◽

C. THOMINIAUX ◽

...

Keyword(s):

Michael Addition ◽

Asymmetric Michael Addition ◽

Chiral Imines

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