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Literature DB >> 14653667

Chiral alpha,beta-dialkoxy- and alpha-alkoxy-beta-aminostannanes: preparation and copper-mediated cross-coupling.

Suchismita Mohapatra¹, A Bandyopadhyay, D K Barma, Jorge H Capdevila, J R Falck.

Abstract

Addition of Zn(n-Bu(3)Sn)(2) to prochiral aldehydes affords anti-alpha,beta-dialkoxy- and anti-alpha-alkoxy-beta-aminostannanes in good yield (up to 77%) and excellent diastereoselectivity (up to 98% de). syn-Isomers are accessed from the initial adducts via Mitsunobu inversion/saponification. The corresponding thionocarbamates undergo mild Cu(I)-mediated cross-coupling with a variety of organic halides, inter alia, allylic, cinnamylic, propargylic, and acetylenic, with retention of configuration. [reaction: see text]

Entities: Chemical Gene

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Year: 2003 PMID： 14653667 DOI： 10.1021/ol035458v

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

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Cited

12 in total

Review 1. Enantioselective and Enantiospecific Transition-Metal-Catalyzed Cross-Coupling Reactions of Organometallic Reagents To Construct C-C Bonds.

Authors: Alan H Cherney; Nathaniel T Kadunce; Sarah E Reisman
Journal: Chem Rev Date: 2015-08-13 Impact factor: 60.622

2. Synthesis of enantioenriched alpha-(hydroxyalkyl)-tri-n-butylstannanes.

Authors: Anyu He; John R Falck
Journal: Angew Chem Int Ed Engl Date: 2008 Impact factor: 15.336

3. Stereocontrolled synthesis of α-amino-α'-alkoxy ketones by a copper-catalyzed cross-coupling of peptidic thiol esters and α-alkoxyalkylstannanes.

Authors: Hao Li; Anyu He; John R Falck; Lanny S Liebeskind
Journal: Org Lett Date: 2011-06-15 Impact factor: 6.005

10. Configurationally Stable, Enantioenriched Organometallic Nucleophiles in Stereospecific Pd-Catalyzed Cross-Coupling Reactions: An Alternative Approach to Asymmetric Synthesis.

Authors: Chao-Yuan Wang; Joseph Derosaa; Mark R Biscoe
Journal: Chem Sci Date: 2015 Impact factor: 9.825

Chiral alpha,beta-dialkoxy- and alpha-alkoxy-beta-aminostannanes: preparation and copper-mediated cross-coupling.

Review 1. Enantioselective and Enantiospecific Transition-Metal-Catalyzed Cross-Coupling Reactions of Organometallic Reagents To Construct C-C Bonds.

2. Synthesis of enantioenriched alpha-(hydroxyalkyl)-tri-n-butylstannanes.

3. Stereocontrolled synthesis of α-amino-α'-alkoxy ketones by a copper-catalyzed cross-coupling of peptidic thiol esters and α-alkoxyalkylstannanes.

4. A General Approach to Stereospecific Cross-Coupling Reactions of Nitrogen-Containing Stereocenters.

5. Rethinking Carbohydrate Synthesis: Stereoretentive Reactions of Anomeric Stannanes.

6. Pd-catalyzed cross-coupling of α-(acyloxy)-tri-n-butylstannanes with alkenyl, aryl, and heteroaryl electrophiles.

7. Stereoselectivity in Pd-catalysed cross-coupling reactions of enantioenriched nucleophiles.

8. Epoxygenase eicosanoids: synthesis of tetrahydrofuran-diol metabolites and their vasoactivity.

9. Stereoretentive Pd-catalysed Stille cross-coupling reactions of secondary alkyl azastannatranes and aryl halides.

10. Configurationally Stable, Enantioenriched Organometallic Nucleophiles in Stereospecific Pd-Catalyzed Cross-Coupling Reactions: An Alternative Approach to Asymmetric Synthesis.