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Literature DB >> 25738419

Catalytic chemo-, regio-, and enantioselective bromochlorination of allylic alcohols.

Dennis X Hu¹, Frederick J Seidl¹, Cyril Bucher¹, Noah Z Burns¹.

Abstract

Herein we describe a highly chemo-, regio-, and enantioselective bromochlorination reaction of allylic alcohols, employing readily available halogen sources and a simple Schiff base as the chiral catalyst. The application of this interhalogenation reaction to a variety of substrates, the rapid enantioselective synthesis of a bromochlorinated natural product, and preliminary extension of this chemistry to dibromination and dichlorination are reported.

Entities: Chemical

Year: 2015 PMID： 25738419 DOI： 10.1021/jacs.5b01384

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

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Cited

25 in total

1. Organoselenium-catalyzed enantioselective syn-dichlorination of unbiased alkenes.

Authors: Bradley B Gilbert; Stanley T-C Eey; Pavel Ryabchuk; Olivia Garry; Scott E Denmark
Journal: Tetrahedron Date: 2019-06-01 Impact factor: 2.457

2. Dative Directing Group Effects in Ti-Catalyzed [2+2+1] Pyrrole Synthesis: Chemo- and Regioselective Alkyne Heterocoupling.

Authors: Hsin-Chun Chiu; Xin Yi See; Ian A Tonks
Journal: ACS Catal Date: 2018-11-29 Impact factor: 13.084

3. Catalytic Regio- and Enantioselective Haloazidation of Allylic Alcohols.

Authors: Frederick J Seidl; Chang Min; Jovan A Lopez; Noah Z Burns
Journal: J Am Chem Soc Date: 2018-11-12 Impact factor: 15.419

4. Asymmetric Synthesis of Gonytolide A: Strategic Use of an Aryl Halide Blocking Group for Oxidative Coupling.

Authors: Xiaowei Wu; Takayuki Iwata; Adam Scharf; Tian Qin; Kyle D Reichl; John A Porco
Journal: J Am Chem Soc Date: 2018-04-25 Impact factor: 15.419

5. Highly Selective Synthesis of Halomon, Plocamenone, and Isoplocamenone.

Authors: Cyril Bucher; Richard M Deans; Noah Z Burns
Journal: J Am Chem Soc Date: 2015-09-29 Impact factor: 15.419

6. Catalytic Enantioselective Dihalogenation and the Selective Synthesis of (-)-Deschloromytilipin A and (-)-Danicalipin A.

Authors: Matthew L Landry; Dennis X Hu; Grace M McKenna; Noah Z Burns
Journal: J Am Chem Soc Date: 2016-04-08 Impact factor: 15.419

Catalytic chemo-, regio-, and enantioselective bromochlorination of allylic alcohols.

1. Organoselenium-catalyzed enantioselective syn-dichlorination of unbiased alkenes.

2. Dative Directing Group Effects in Ti-Catalyzed [2+2+1] Pyrrole Synthesis: Chemo- and Regioselective Alkyne Heterocoupling.

3. Catalytic Regio- and Enantioselective Haloazidation of Allylic Alcohols.

4. Asymmetric Synthesis of Gonytolide A: Strategic Use of an Aryl Halide Blocking Group for Oxidative Coupling.

5. Highly Selective Synthesis of Halomon, Plocamenone, and Isoplocamenone.

6. Catalytic Enantioselective Dihalogenation and the Selective Synthesis of (-)-Deschloromytilipin A and (-)-Danicalipin A.

Review 7. Catalytic Enantioselective Dihalogenation in Total Synthesis.

8. Enantiospecific Solvolytic Functionalization of Bromochlorides.

9. Triphosgene-pyridine mediated stereoselective chlorination of acyclic aliphatic 1,3-diols.

10. A Unified Approach for the Enantioselective Synthesis of the Brominated Chamigrene Sesquiterpenes.