Literature DB >> 15571388

Stille coupling of stereochemically defined alpha-sulfonamidoorganostannanes.

Kevin W Kells1, J Michael Chong.   

Abstract

Addition of tributylstannylmetallics to (R)-tert-butanesulfonimine derivatives of arylaldehydes provides alpha-sulfinamidostannanes with high (>98% de) diastereoselectivities. Oxidation of these compounds with m-CPBA gives alpha-sulfonamidostannanes which undergo Pd/Cu-catalyzed Stille-type couplings with benzoyl chloride. Best yields are achieved using the electron-rich tris(2,4,6-trimethoxyphenyl)phosphine as the ligand. Inversion of configuration at the benzylic carbon is observed.

Entities:  

Year:  2004        PMID： 15571388     DOI： 10.1021/ja044354s

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  16 in total

1.  Stereospecific cross-coupling of secondary alkyl β-trifluoroboratoamides.

Authors:  Deidre L Sandrock; Ludivine Jean-Gérard; Cheng-yi Chen; Spencer D Dreher; Gary A Molander
Journal:  J Am Chem Soc       Date:  2010-11-15       Impact factor: 15.419

Review 2.  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

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

4.  Stereospecific Palladium-Catalyzed Acylation of Enantioenriched Alkylcarbastannatranes: A General Alternative to Asymmetric Enolate Reactions.

Authors:  Chao-Yuan Wang; Glenn Ralph; Joseph Derosa; Mark R Biscoe
Journal:  Angew Chem Int Ed Engl       Date:  2016-12-16       Impact factor: 15.336

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

Authors:  Xinghua Ma; Haoran Zhao; Meruyert Binayeva; Glenn Ralph; Mohamed Diane; Shibin Zhao; Chao-Yuan Wang; Mark R Biscoe
Journal:  Chem       Date:  2020-03-02       Impact factor: 22.804

6.  Stereospecific cross-coupling of alpha-(thiocarbamoyl)organostannanes with alkenyl, aryl, and heteroaryl iodides.

Authors:  J R Falck; Paresh K Patel; Anish Bandyopadhyay
Journal:  J Am Chem Soc       Date:  2007-01-31       Impact factor: 15.419

7.  Retention or inversion in stereospecific nickel-catalyzed cross-coupling of benzylic carbamates with arylboronic esters: control of absolute stereochemistry with an achiral catalyst.

Authors:  Michael R Harris; Luke E Hanna; Margaret A Greene; Curtis E Moore; Elizabeth R Jarvo
Journal:  J Am Chem Soc       Date:  2013-02-22       Impact factor: 15.419

8.  Asymmetric transition metal-catalyzed cross-coupling reactions for the construction of tertiary stereocenters.

Authors:  Elizabeth C Swift; Elizabeth R Jarvo
Journal:  Tetrahedron       Date:  2013-07-22       Impact factor: 2.457

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

Authors:  Mohan Goli; Anyu He; J R Falck
Journal:  Org Lett       Date:  2010-12-09       Impact factor: 6.005

10.  Synthesis and Suzuki-Miyaura Cross-Coupling of Enantioenriched Secondary Potassium β-Trifluoroboratoamides: Catalytic, Asymmetric Conjugate Addition of Bisboronic Acid and Tetrakis(dimethylamino)diboron to α,β-Unsaturated Carbonyl Compounds.

Authors:  Gary A Molander; Steven R Wisniewski; Mona Hosseini-Sarvari
Journal:  Adv Synth Catal       Date:  2013-10-11       Impact factor: 5.837
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.