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Literature DB >> 19159255

Mitsunobu approach to the synthesis of optically active alpha,alpha-disubstituted amino acids.

Jonathan E Green¹, David M Bender, Stona Jackson, Martin J O'Donnell, James R McCarthy.

Abstract

Chiral tertiary alpha-hydroxy esters of known stereochemical configuration were transformed to alpha-azido esters by Mitsunobu reaction with HN3. Optimization of this reaction was shown to proceed at room temperature with high chemical yield using 1,1-(azodicarbonyl)dipiperidine (ADDP) and trimethylphosphine (PMe3). Complete inversion of configuration was observed at the alpha-carbon. Several alpha,alpha-disubstituted amino acids were synthesized in high overall chemical yield and optical purity.

Entities: Chemical Gene

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Year: 2009 PMID： 19159255 DOI： 10.1021/ol802325h

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

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Cited

8 in total

1. Synthesis of diarylmethylamines via palladium-catalyzed regioselective arylation of 1,1,3-triaryl-2-azaallyl anions.

Authors: Minyan Li; Baris Yücel; Javier Adrio; Ana Bellomo; Patrick J Walsh
Journal: Chem Sci Date: 2014-06-01 Impact factor: 9.825

2. Synthesis of Chiral Nonracemic Tertiary α-Thio and α-Sulfonyl Acetic Esters via S(N)2 reactions of Tertiary Mesylates.

Authors: Jimmie D Weaver; David K Morris; Jon A Tunge
Journal: Synlett Date: 2010-02-01 Impact factor: 2.454

3. Dissecting the influence of oxazolidinones and cyclic carbonates in sialic acid chemistry.

Authors: Pavan K Kancharla; Chandrasekhar Navuluri; David Crich
Journal: Angew Chem Int Ed Engl Date: 2012-09-13 Impact factor: 15.336

4. Development of the enantioselective addition of ethyl diazoacetate to aldehydes: asymmetric synthesis of 1,2-diols.

Authors: Barry M Trost; Sushant Malhotra; Philipp Koschker; Pascal Ellerbrock
Journal: J Am Chem Soc Date: 2012-01-18 Impact factor: 15.419

5. Double nucleophilic addition to iminomalonate, leading to the synthesis of quaternary α-amino diesters and desymmetrization of the products.

Authors: Makoto Shimizu; Miki Mushika; Isao Mizota; Yusong Zhu
Journal: RSC Adv Date: 2019-07-29 Impact factor: 4.036

Mitsunobu approach to the synthesis of optically active alpha,alpha-disubstituted amino acids.

1. Synthesis of diarylmethylamines via palladium-catalyzed regioselective arylation of 1,1,3-triaryl-2-azaallyl anions.

2. Synthesis of Chiral Nonracemic Tertiary α-Thio and α-Sulfonyl Acetic Esters via S(N)2 reactions of Tertiary Mesylates.

3. Dissecting the influence of oxazolidinones and cyclic carbonates in sialic acid chemistry.

4. Development of the enantioselective addition of ethyl diazoacetate to aldehydes: asymmetric synthesis of 1,2-diols.

5. Double nucleophilic addition to iminomalonate, leading to the synthesis of quaternary α-amino diesters and desymmetrization of the products.

6. Iron-catalyzed carboazidation of alkenes and alkynes.

7. Stereoinvertive Nucleophilic Substitution at Quaternary Carbon Stereocenters of Cyclopropyl Ketones and Ethers.

Review 8. Stereospecific nucleophilic substitution at tertiary and quaternary stereocentres.