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Literature DB >> 12182574

Diastereoselective reduction of alkenylboronic esters as a new method for controlling the stereochemistry of up to three adjacent centers in cyclic and acyclic molecules.

Abstract

[reaction: see text] cis-Boronates are readily available via a diastereoselective Pd-catalyzed reduction of tetrasubstituted alkenylboronic esters using H2. Applying the reaction conditions presented to unsaturated open-chain boronic esters allows the stereochemistry of up to three adjacent centers to be controlled.

Entities: Chemical Disease

Year: 2002 PMID： 12182574 DOI： 10.1021/ol0262486

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

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Cited

9 in total

1. Nickel-Catalyzed Arylboration of Cyclopentene.

Authors: Stephen R Sardini; M Kevin Brown
Journal: Organic Synth Date: 2020

2. Nickel-Catalyzed Stereoselective Arylboration of Unactivated Alkenes.

Authors: Kaitlyn M Logan; Stephen R Sardini; Sean D White; M Kevin Brown
Journal: J Am Chem Soc Date: 2017-12-22 Impact factor: 15.419

3. Direct stereospecific amination of alkyl and aryl pinacol boronates.

Authors: Scott N Mlynarski; Alexander S Karns; James P Morken
Journal: J Am Chem Soc Date: 2012-09-24 Impact factor: 15.419

4. Efficient C-B bond formation promoted by N-heterocyclic carbenes: synthesis of tertiary and quaternary B-substituted carbons through metal-free catalytic boron conjugate additions to cyclic and acyclic alpha,beta-unsaturated carbonyls.

Authors: Kang-sang Lee; Adil R Zhugralin; Amir H Hoveyda
Journal: J Am Chem Soc Date: 2009-06-03 Impact factor: 15.419

Diastereoselective reduction of alkenylboronic esters as a new method for controlling the stereochemistry of up to three adjacent centers in cyclic and acyclic molecules.

1. Nickel-Catalyzed Arylboration of Cyclopentene.

2. Nickel-Catalyzed Stereoselective Arylboration of Unactivated Alkenes.

3. Direct stereospecific amination of alkyl and aryl pinacol boronates.

4. Efficient C-B bond formation promoted by N-heterocyclic carbenes: synthesis of tertiary and quaternary B-substituted carbons through metal-free catalytic boron conjugate additions to cyclic and acyclic alpha,beta-unsaturated carbonyls.

5. Radical Aryl Migration from Boron to Carbon.

6. Simple access to elusive α-boryl carbanions and their alkylation: an umpolung construction for organic synthesis.

7. Transition Metal-Free 1,2-Carboboration of Unactivated Alkenes.

8. Controlled partial transfer hydrogenation of quinolines by cobalt-amido cooperative catalysis.

9. Enantioselective Copper-Catalyzed Synthesis of Trifluoromethyl-Cyclopropylboronates.