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Literature DB >> 20681608

Development of a 2-aza-Cope-[3 + 2] dipolar cycloaddition strategy for the synthesis of quaternary proline scaffolds.

Michael P McCormack¹, Tamila Shalumova, Joseph M Tanski, Stephen P Waters.

Abstract

A one-pot multicomponent procedure for the synthesis of highly functionalized pyrrolidine rings through a domino 2-aza-Cope-[3 + 2] dipolar cycloaddition sequence has been demonstrated. This protocol was found to be both high-yielding and stereoselective for the endo cycloadduct.

Entities: Chemical

Mesh：

Substances：
Pyrrolidines
Proline

Year: 2010 PMID： 20681608 PMCID： PMC2929309 DOI： 10.1021/ol101606v

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

18 in total

1. Tandem Reactions in Organic Synthesis: Novel Strategies for Natural Product Elaboration and the Development of New Synthetic Methodology.

Authors: Philip J. Parsons; Clive S. Penkett; Adrian J. Shell
Journal: Chem Rev Date: 1996-02-01 Impact factor: 60.622

2. Molecular Rearrangements in the Construction of Complex Molecules.

Authors: Larry E Overman
Journal: Tetrahedron Date: 2009-09-15 Impact factor: 2.457

3. A formal total synthesis of (-)-FR901483, using a tandem cationic aza-Cope rearrangement/Mannich cyclization approach.

Authors: Kay M Brummond; Sang-phyo Hong
Journal: J Org Chem Date: 2005-02-04 Impact factor: 4.354

4. Intramolecular dipolar cycloaddition reactions of azomethine ylides.

Authors: Iain Coldham; Richard Hufton
Journal: Chem Rev Date: 2005-07 Impact factor: 60.622

5. Neighboring group-controlled hydrolysis: towards "designer" drug release biomaterials.

Authors: Colin P McCoy; Ryan J Morrow; Christopher R Edwards; David S Jones; Sean P Gorman
Journal: Bioconjug Chem Date: 2007 Jan-Feb Impact factor: 4.774

6. Construction of enantiopure pyrrolidine ring system via asymmetric [3+2]-cycloaddition of azomethine ylides.

Authors: Ganesh Pandey; Prabal Banerjee; Smita R Gadre
Journal: Chem Rev Date: 2006-11 Impact factor: 60.622

7. Highly enantioselective Ag(i)-catalyzed [3 + 2] cycloaddition of azomethine ylides.

Authors: James M Longmire; Bin Wang; Xumu Zhang
Journal: J Am Chem Soc Date: 2002-11-13 Impact factor: 15.419

8. Efficient enantiomeric synthesis of pyrrolidine and piperidine alkaloids from tobacco.

Authors: F X Felpin; S Girard; G Vo-Thanh; R J Robins; J Villiéras; J Lebreton
Journal: J Org Chem Date: 2001-09-21 Impact factor: 4.354

9. Catalytic asymmetric [3+2] cycloaddition of azomethine ylides. Development of a versatile stepwise, three-component reaction for diversity-oriented synthesis.

Authors: Chuo Chen; Xiaodong Li; Stuart L Schreiber
Journal: J Am Chem Soc Date: 2003-08-27 Impact factor: 15.419

Development of a 2-aza-Cope-[3 + 2] dipolar cycloaddition strategy for the synthesis of quaternary proline scaffolds.

1. Tandem Reactions in Organic Synthesis: Novel Strategies for Natural Product Elaboration and the Development of New Synthetic Methodology.

2. Molecular Rearrangements in the Construction of Complex Molecules.

3. A formal total synthesis of (-)-FR901483, using a tandem cationic aza-Cope rearrangement/Mannich cyclization approach.

4. Intramolecular dipolar cycloaddition reactions of azomethine ylides.

5. Neighboring group-controlled hydrolysis: towards "designer" drug release biomaterials.

6. Construction of enantiopure pyrrolidine ring system via asymmetric [3+2]-cycloaddition of azomethine ylides.

7. Highly enantioselective Ag(i)-catalyzed [3 + 2] cycloaddition of azomethine ylides.

8. Efficient enantiomeric synthesis of pyrrolidine and piperidine alkaloids from tobacco.

9. Catalytic asymmetric [3+2] cycloaddition of azomethine ylides. Development of a versatile stepwise, three-component reaction for diversity-oriented synthesis.

10. Total synthesis of (+/-)-actinophyllic acid.

Review 1. Toward a symphony of reactivity: cascades involving catalysis and sigmatropic rearrangements.

2. An aza-Prins cyclization approach to functionalized indolizidines from 2-allylpyrrolidines.

3. Synthesis of functionalized indolizidines through Pauson-Khand cycloaddition of 2-allylpyrrolidines.

4. Lewis acidic FeCl₃ promoted 2-aza-Cope rearrangement to afford α-substituted homoallylamines in dimethyl carbonate.

5. A new entry to azomethine ylides from allylic amines and glyoxals: shifting the reliance on amino ester precursors.