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Literature DB >> 19684878

Synthesis of Functionalized Isoindolinones: Addition of In Situ Generated Organoalanes to Acyliminium Ions.

Joshua G Pierce¹, David L Waller, Peter Wipf.

Abstract

Addition of in situ generated di- or trisubstituted alkenylalanes to N-acyliminium ions provides rapid access to functionalized isoindolinones. Subsequent ring closing metathesis leads to tricyclic products. These transformations proceed under mild conditions and allow for the convergent synthesis of biologically significant scaffolds from readily available starting materials.

Entities: Chemical

Year: 2007 PMID： 19684878 PMCID： PMC2726970 DOI： 10.1016/j.jorganchem.2007.05.035

Source DB: PubMed Journal: J Organomet Chem ISSN： 0022-328X Impact factor: 2.369

18 in total

1. Olefin Metathesis and Beyond A list of abbreviations can be found at the end of this article.

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

2. Concise formal synthesis of (-)-peduncularine via ring-closing metathesis.

Authors: David G Washburn; Richard W Heidebrecht; Stephen F Martin
Journal: Org Lett Date: 2003-09-18 Impact factor: 6.005

3. Asymmetric synthesis of 3-substituted isoindolinones: application to the total synthesis of (+)-lennoxamine.

Authors: Daniel L Comins; Stefan Schilling; Yanchen Zhang
Journal: Org Lett Date: 2005-01-06 Impact factor: 6.005

4. Regioselective and diastereoselective amination of polybenzyl ethers using chlorosulfonyl isocyanate: total syntheses of 1,4-dideoxy-1,4-imino-D-arabinitol and (-)-lentiginosine.

Authors: In Su Kim; Ok Pyo Zee; Young Hoon Jung
Journal: Org Lett Date: 2006-08-31 Impact factor: 6.005

5. Isoindol-1-one analogues of 4-(2'-methoxyphenyl)-1-[2'-[N-(2"-pyridyl)-p-iodobenzamido]ethyl]pipera zine (p-MPPI) as 5-HT1A receptor ligands.

Authors: Z P Zhuang; M P Kung; M Mu; H F Kung
Journal: J Med Chem Date: 1998-01-15 Impact factor: 7.446

6. Highly regioselective radical cyclizations of allenamides.

Authors: Lichun Shen; Richard P Hsung
Journal: Org Lett Date: 2005-03-03 Impact factor: 6.005

7. Expedient synthesis of the alpha-C-glycoside analogue of the immunostimulant galactosylceramide (KRN7000).

Authors: Peter Wipf; Joshua G Pierce
Journal: Org Lett Date: 2006-07-20 Impact factor: 6.005

8. Transition-metal-mediated cascade reactions: the water-accelerated carboalumination-Claisen rearrangement-carbonyl addition reaction.

Authors: Peter Wipf; David L Waller; Jonathan T Reeves
Journal: J Org Chem Date: 2005-09-30 Impact factor: 4.354

Synthesis of Functionalized Isoindolinones: Addition of In Situ Generated Organoalanes to Acyliminium Ions.

1. Olefin Metathesis and Beyond A list of abbreviations can be found at the end of this article.

2. Concise formal synthesis of (-)-peduncularine via ring-closing metathesis.

3. Asymmetric synthesis of 3-substituted isoindolinones: application to the total synthesis of (+)-lennoxamine.

4. Regioselective and diastereoselective amination of polybenzyl ethers using chlorosulfonyl isocyanate: total syntheses of 1,4-dideoxy-1,4-imino-D-arabinitol and (-)-lentiginosine.

5. Isoindol-1-one analogues of 4-(2'-methoxyphenyl)-1-[2'-[N-(2"-pyridyl)-p-iodobenzamido]ethyl]pipera zine (p-MPPI) as 5-HT1A receptor ligands.

6. Highly regioselective radical cyclizations of allenamides.

7. Expedient synthesis of the alpha-C-glycoside analogue of the immunostimulant galactosylceramide (KRN7000).

8. Transition-metal-mediated cascade reactions: the water-accelerated carboalumination-Claisen rearrangement-carbonyl addition reaction.

9. Silver(I)-catalyzed addition of zirconocenes to glycal epoxides. A new synthesis of alpha-C-glycosides.

10. Synthesis of bridged azabicyclic structures via ring-closing olefin metathesis.

1. Titanocene(III)-catalyzed formation of indolines and azaindolines.

2. A microwave assisted intramolecular-furan-Diels-Alder approach to 4-substituted indoles.

3. Synthesis of a library of tricyclic azepinoisoindolinones.

4. Unprecedented selective homogeneous cobalt-catalysed reductive alkoxylation of cyclic imides under mild conditions.