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Literature DB >> 24416631

Chiral β-Iodoamines by Urea-Catalyzed Iodocyclization of Trichloroacetimidates.

Cheyenne S Brindle¹, Charles S Yeung¹, Eric N Jacobsen¹.

Abstract

Highly enantioselective vicinal iodoamination of olefins is accomplished through the iodocyclization of alkenyl trichloroacetimidates catalyzed by a new chiral Schiff-base urea derivative. The resulting products are converted readily to a variety of polyfunctional amine-containing chiral building blocks.

Entities: Chemical Gene

Year: 2013 PMID： 24416631 PMCID： PMC3885344 DOI： 10.1039/C3SC50410G

Source DB: PubMed Journal: Chem Sci J ISSN： 2150-3494

32 in total

1. Asymmetric electrophilic fluorination using an anionic chiral phase-transfer catalyst.

Authors: Vivek Rauniyar; Aaron D Lackner; Gregory L Hamilton; F Dean Toste
Journal: Science Date: 2011-12-23 Impact factor: 47.728

2. Catalytic asymmetric chloroamination reaction of α,β-unsaturated γ-keto esters and chalcones.

Authors: Yunfei Cai; Xiaohua Liu; Jun Jiang; Weiliang Chen; Lili Lin; Xiaoming Feng
Journal: J Am Chem Soc Date: 2011-03-28 Impact factor: 15.419

3. Enantioselective, palladium-catalyzed α-arylation of N-Boc pyrrolidine: in situ react IR spectroscopic monitoring, scope, and synthetic applications.

Authors: Graeme Barker; Julia L McGrath; Artis Klapars; Darren Stead; George Zhou; Kevin R Campos; Peter O'Brien
Journal: J Org Chem Date: 2011-07-08 Impact factor: 4.354

4. Highly enantioselective electrophilic α-bromination of enecarbamates: chiral phosphoric acid and calcium phosphate salt catalysts.

Authors: Aurélien Alix; Claudia Lalli; Pascal Retailleau; Géraldine Masson
Journal: J Am Chem Soc Date: 2012-06-14 Impact factor: 15.419

Review 5. Catalytic, asymmetric halofunctionalization of alkenes--a critical perspective.

Authors: Scott E Denmark; William E Kuester; Matthew T Burk
Journal: Angew Chem Int Ed Engl Date: 2012-09-25 Impact factor: 15.336

6. Enantioselective bromoaminocyclization using amino-thiocarbamate catalysts.

Authors: Ling Zhou; Jie Chen; Chong Kiat Tan; Ying-Yeung Yeung
Journal: J Am Chem Soc Date: 2011-05-03 Impact factor: 15.419

7. Enantioselective bromolactonization of conjugated (Z)-enynes.

Authors: Wei Zhang; Suqing Zheng; Na Liu; Jenny B Werness; Ilia A Guzei; Weiping Tang
Journal: J Am Chem Soc Date: 2010-03-24 Impact factor: 15.419

8. Enantioselective, thiourea-catalyzed intermolecular addition of indoles to cyclic N-acyl iminium ions.

Authors: Emily A Peterson; Eric N Jacobsen
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336

9. Thiourea-catalyzed enantioselective hydrophosphonylation of imines: practical access to enantiomerically enriched alpha-amino phosphonic acids.

Authors: Guy D Joly; Eric N Jacobsen
Journal: J Am Chem Soc Date: 2004-04-07 Impact factor: 15.419

Chiral β-Iodoamines by Urea-Catalyzed Iodocyclization of Trichloroacetimidates.

1. Asymmetric electrophilic fluorination using an anionic chiral phase-transfer catalyst.

2. Catalytic asymmetric chloroamination reaction of α,β-unsaturated γ-keto esters and chalcones.

3. Enantioselective, palladium-catalyzed α-arylation of N-Boc pyrrolidine: in situ react IR spectroscopic monitoring, scope, and synthetic applications.

4. Highly enantioselective electrophilic α-bromination of enecarbamates: chiral phosphoric acid and calcium phosphate salt catalysts.

Review 5. Catalytic, asymmetric halofunctionalization of alkenes--a critical perspective.

6. Enantioselective bromoaminocyclization using amino-thiocarbamate catalysts.

7. Enantioselective bromolactonization of conjugated (Z)-enynes.

8. Enantioselective, thiourea-catalyzed intermolecular addition of indoles to cyclic N-acyl iminium ions.

9. Thiourea-catalyzed enantioselective hydrophosphonylation of imines: practical access to enantiomerically enriched alpha-amino phosphonic acids.

10. Enantioselective halocyclization using reagents tailored for chiral anion phase-transfer catalysis.

1. Enantioselective small molecule synthesis by carbon dioxide fixation using a dual Brønsted acid/base organocatalyst.

2. Association of Halogen Bonding and Hydrogen Bonding in Metal Acetate-Catalyzed Asymmetric Halolactonization.

3. Absolute and relative facial selectivities in organocatalytic asymmetric chlorocyclization reactions.

4. Chiral ion-pair organocatalyst promotes highly enantioselective 3-exo iodo-cycloetherification of allyl alcohols.