Warning: Undefined array key "mm" in /www/wwwroot/www.ai-bt.com/si.php on line 10 Deprecated: trim(): Passing null to parameter #1 ($string) of type string is deprecated in /www/wwwroot/www.ai-bt.com/si.php on line 10 Ester Formation via Symbiotic Activation Utilizing Trichloroacetimidate Electrophiles.

Literature DB >> 31117564

Ester Formation via Symbiotic Activation Utilizing Trichloroacetimidate Electrophiles.

Nivedita S Mahajani¹, Rowan I L Meador¹, Tomas J Smith¹, Sarah E Canarelli¹, Arijit A Adhikari¹, Jigisha P Shah¹, Christopher M Russo¹, Daniel R Wallach¹, Kyle T Howard¹, Alexandra M Millimaci¹, John D Chisholm¹.

Abstract

Trichloroacetimidates are useful reagents for the synthesis of esters under mild conditions that do not require an exogenous promoter. These conditions avoid the undesired decomposition of substrates with sensitive functional groups that are often observed with the use of strong Lewis or Brønsted acids. With heating, these reactions have been extended to benzyl esters without electron-donating groups. These inexpensive and convenient methods should find application in the formation of esters in complex substrates.

Entities: Chemical Disease Species

Year: 2019 PMID： 31117564 PMCID： PMC6597275 DOI： 10.1021/acs.joc.9b00745

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

46 in total

1. Stereoselective total synthesis of ent-EI-1941-2 and Epi-ent-EI-1941-2.

Authors: Mitsuru Shoji; Takao Uno; Yujiro Hayashi
Journal: Org Lett Date: 2004-11-25 Impact factor: 6.005

2. Diazoalkanes in peptide semisynthesis.

Authors: R E Offord; H T Storey; A R Rees; C F Hayward; W H Johnson; M H Pheasey; D A Wightman
Journal: Biochem J Date: 1976-12-01 Impact factor: 3.857

3. Convenient access to glutamic acid side chain homologues compatible with solid phase peptide synthesis.

Authors: Shannon J Ryan; Yongda Zhang; Alan J Kennan
Journal: Org Lett Date: 2005-10-13 Impact factor: 6.005

4. Synthesis of the macrocyclic core of laulimalide.

Authors: I Paterson; C De Savi; M Tudge
Journal: Org Lett Date: 2001-01-25 Impact factor: 6.005

5. Enantio- and diastereoselective total synthesis of EI-1941-1, -2, and -3, inhibitors of interleukin-1beta converting enzyme, and biological properties of their derivatives.

Authors: Mitsuru Shoji; Takao Uno; Hideaki Kakeya; Rie Onose; Isamu Shiina; Hiroyuki Osada; Yujiro Hayashi
Journal: J Org Chem Date: 2005-11-25 Impact factor: 4.354

6. A short synthesis and biological evaluation of potent and nontoxic antimalarial bridged bicyclic beta-sulfonyl-endoperoxides.

Authors: Mario D Bachi; Edward E Korshin; Roland Hoos; Alex M Szpilman; Poonsakdi Ploypradith; Suji Xie; Theresa A Shapiro; Gary H Posner
Journal: J Med Chem Date: 2003-06-05 Impact factor: 7.446

7. A general procedure for the esterification of carboxylic acids with diazoalkanes generated in situ by the oxidation of N-tert-butyldimethylsilylhydrazones with (difluoroiodo)benzene.

Authors: Michael E Furrow; Andrew G Myers
Journal: J Am Chem Soc Date: 2004-10-06 Impact factor: 15.419

8. High-load, ROMP-generated oligomeric bis-acid chlorides: design of soluble and insoluble nucleophile scavengers.

Authors: Joel D Moore; Robert J Byrne; Punitha Vedantham; Daniel L Flynn; Paul R Hanson
Journal: Org Lett Date: 2003-11-13 Impact factor: 6.005

9. Enantioselective separation of racemic juvenile hormone III by normal-phase high-performance liquid chromatography and preparation of [(2)H(3)]juvenile hormone III as an internal standard for liquid chromatography-mass spectrometry quantification.

Authors: Akio Ichikawa; Hiroshi Ono; Kenjiro Furuta; Takahiro Shiotsuki; Tetsuro Shinoda
Journal: J Chromatogr A Date: 2007-06-07 Impact factor: 4.759

Ester Formation via Symbiotic Activation Utilizing Trichloroacetimidate Electrophiles.

1. Stereoselective total synthesis of ent-EI-1941-2 and Epi-ent-EI-1941-2.

2. Diazoalkanes in peptide semisynthesis.

3. Convenient access to glutamic acid side chain homologues compatible with solid phase peptide synthesis.

4. Synthesis of the macrocyclic core of laulimalide.

5. Enantio- and diastereoselective total synthesis of EI-1941-1, -2, and -3, inhibitors of interleukin-1beta converting enzyme, and biological properties of their derivatives.

6. A short synthesis and biological evaluation of potent and nontoxic antimalarial bridged bicyclic beta-sulfonyl-endoperoxides.

7. A general procedure for the esterification of carboxylic acids with diazoalkanes generated in situ by the oxidation of N-tert-butyldimethylsilylhydrazones with (difluoroiodo)benzene.

8. High-load, ROMP-generated oligomeric bis-acid chlorides: design of soluble and insoluble nucleophile scavengers.

9. Enantioselective separation of racemic juvenile hormone III by normal-phase high-performance liquid chromatography and preparation of [(2)H(3)]juvenile hormone III as an internal standard for liquid chromatography-mass spectrometry quantification.

10. Microwave-accelerated O-alkylation of carboxylic acids with O-alkylisoureas.

1. Dialkylation of Indoles with Trichloroacetimidates to Access 3,3-Disubstituted Indolenines.

2. Substrate-Controlled Cu(OAc)₂-Catalyzed Stereoselective Semi-Reduction of Alkynes with MeOH as the Hydrogen Source.

3. Formation of Pyrroloindolines via the Alkylation of Tryptamines with Trichloroacetimidates.

4. An Efficient Metal-Free Oxidative Esterification and Amination of Benzyl C-H Bond.