Literature DB >> 23139434

Tandem chain extension-Mannich reaction: an approach to β-proline derivatives.

Alexander M Jacobine1, Angela L A Puchlopek, Charles K Zercher, Jon B Briggs, Jerry P Jasinski, Raymond J Butcher.   

Abstract

A zinc carbenoid-initiated chain extension reaction provides access to an organometallic intermediate, which can be used to capture activated imines. Deprotection of the nitrogen and reduction provides access to racemic derivatives of β-proline. The relative stereochemistry of the β-proline can be controlled through use of different activating groups on the imine nitrogen.

Entities:  

Year:  2012        PMID： 23139434      PMCID： PMC3489501          DOI： 10.1016/j.tet.2012.07.039

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.457


  12 in total

1.  Synthetic routes towards enantiomerically pure beta-amino acids.

Authors:  Norbert Sewald
Journal:  Angew Chem Int Ed Engl       Date:  2003       Impact factor: 15.336

Review 2.  Recent advances in the catalytic asymmetric synthesis of beta-amino acids.

Authors:  Barbara Weiner; Wiktor Szymański; Dick B Janssen; Adriaan J Minnaard; Ben L Feringa
Journal:  Chem Soc Rev       Date:  2010-02-24       Impact factor: 54.564

3.  A mechanistic investigation into the zinc carbenoid-mediated homologation reaction by DFT methods: is a classical donor-acceptor cyclopropane intermediate involved?

Authors:  Wilhelm A Eger; Charles K Zercher; Craig M Williams
Journal:  J Org Chem       Date:  2010-11-05       Impact factor: 4.354

4.  Asymmetric catalytic Mannich reactions catalyzed by urea derivatives: enantioselective synthesis of beta-aryl-beta-amino acids.

Authors:  Anna G Wenzel; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2002-11-06       Impact factor: 15.419

5.  A direct catalytic asymmetric Mannich-type reaction via a dinuclear zinc catalyst: synthesis of either anti- or syn-alpha-hydroxy-beta-amino ketones.

Authors:  Barry M Trost; Jaray Jaratjaroonphong; Vichai Reutrakul
Journal:  J Am Chem Soc       Date:  2006-03-08       Impact factor: 15.419

6.  Tandem chain extension-aldol reaction: syn selectivity with a zinc enolate.

Authors:  S Lai; C K Zercher; J P Jasinski; S N Reid; R J Staples
Journal:  Org Lett       Date:  2001-12-27       Impact factor: 6.005

7.  Chlorotitanium enolate addition to aldimines: a stereoselective route to alpha-oxy-beta-substituted-beta-amino esters.

Authors:  J C Adrian; J L Barkin; R J Fox; J E Chick; A D Hunter; R A Nicklow
Journal:  J Org Chem       Date:  2000-09-22       Impact factor: 4.354

8.  Zinc carbenoid-mediated chain extension: preparation of alpha,beta-unsaturated-gamma-keto esters and amides.

Authors:  Matthew D Ronsheim; Charles K Zercher
Journal:  J Org Chem       Date:  2003-05-30       Impact factor: 4.354

9.  Asymmetric synthesis of polyhydroxy alpha-amino acids with the sulfinimine-mediated asymmetric strecker reaction: 2-amino 2-deoxy L-xylono-1,5-lactone (polyoxamic acid lactone).

Authors:  Franklin A Davis; Kavirayani R Prasad; Patrick J Carroll
Journal:  J Org Chem       Date:  2002-11-01       Impact factor: 4.354

10.  Asymmetric synthesis of beta-amino acid derivatives incorporating a broad range of substitution patterns by enolate additions to tert-butanesulfinyl imines.

Authors:  Tony P Tang; Jonathan A Ellman
Journal:  J Org Chem       Date:  2002-11-01       Impact factor: 4.354
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  2 in total

1.  Tandem Homologation-Acylation Chemistry: Single and Double Homologation.

Authors:  Carley S Henderson; Jennifer R Mazzone; Amanda M Moore; Charles K Zercher
Journal:  Tetrahedron       Date:  2021-05-19       Impact factor: 2.388

2.  Synthetic Approach toward Enantiopure Cyclic Sulfinamides.

Authors:  Glebs Jersovs; Matiss Bojars; Pavel A Donets; Edgars Suna
Journal:  Org Lett       Date:  2022-06-16       Impact factor: 6.072
  2 in total

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