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Literature DB >> 22942479

Intercepted Decarboxylative Allylations of Nitroalkanoates.

Meghan Schmitt¹, Alexander J Grenning, Jon A Tunge.

Abstract

Using palladium-catalyzed decarboxylation, several cascade reactions of allyl and prenyl nitroalkanoates that lead to nitro-containing chemical building blocks are described. A nitronate Michael addition/Tsuji-Trost allylation cascade was developed, leading to functionally dense chemical building blocks. Likewise, a Tsuji-Trost/decarboxylative protonation sequence was developed for the synthesis of orthogonally functionalized 2° nitroalkanes. The latter method provides rapid access to the indolizidine core.

Entities: Chemical Disease Gene

Year: 2012 PMID： 22942479 PMCID： PMC3430473 DOI： 10.1016/j.tetlet.2012.05.138

Source DB: PubMed Journal: Tetrahedron Lett ISSN： 0040-4039 Impact factor: 2.415

29 in total

1. Asymmetric Alkylation of Nitroalkanes We thank the National Science Foundation and the National Institutes of Health (NIH), General Medical Sciences, for their generous support of our programs. Rhône-Poulenc graciously provided a postdoctoral fellowship for J.-P. S. Mass spectra were provided by the Mass Spectrometry Facility of the University of California, San Francisco, supported by the NIH Division of Research Resources.

Authors:
Journal: Angew Chem Int Ed Engl Date: 2000-09-01 Impact factor: 15.336

2. Electrophilicities of trans-β-nitrostyrenes.

Authors: Ivo Zenz; Herbert Mayr
Journal: J Org Chem Date: 2011-10-18 Impact factor: 4.354

3. Synthesis of homoallylic amines via the palladium-catalyzed decarboxylative coupling of amino acid derivatives.

Authors: Erin C Burger; Jon A Tunge
Journal: J Am Chem Soc Date: 2006-08-09 Impact factor: 15.419

4. Ring-contraction strategy for the practical, scalable, catalytic asymmetric synthesis of versatile γ-quaternary acylcyclopentenes.

Authors: Allen Y Hong; Michael R Krout; Thomas Jensen; Nathan B Bennett; Andrew M Harned; Brian M Stoltz
Journal: Angew Chem Int Ed Engl Date: 2011-02-24 Impact factor: 15.336

5. One-pot tandem decarboxylative allylation-Heck cyclization of allyl diphenylglycinate imines: rapid access to polyfunctionalized 1-aminoindanes.

Authors: Wendy H Fields; Ali K Khan; Michal Sabat; Jason J Chruma
Journal: Org Lett Date: 2008-10-29 Impact factor: 6.005

Intercepted Decarboxylative Allylations of Nitroalkanoates.

2. Electrophilicities of trans-β-nitrostyrenes.

3. Synthesis of homoallylic amines via the palladium-catalyzed decarboxylative coupling of amino acid derivatives.

4. Ring-contraction strategy for the practical, scalable, catalytic asymmetric synthesis of versatile γ-quaternary acylcyclopentenes.

5. One-pot tandem decarboxylative allylation-Heck cyclization of allyl diphenylglycinate imines: rapid access to polyfunctionalized 1-aminoindanes.

6. Rapid decarboxylative allylation of nitroalkanes.

7. Decarboxylative allylation using sulfones as surrogates of alkanes.

8. Regiospecific decarboxylative allylation of nitriles.

9. Asymmetric cycloadditions of palladium-polarized aza-o-xylylenes.

10. C-C bond-forming reactions via Pd-mediated decarboxylative alpha-imino anion generation.

1. Prenyl Praxis: A Method for Direct Photocatalytic Defluoroprenylation.