scholarly journals Catalytic Enantioselective Alkylation of Indoles with trans-4-Methylthio-β-Nitrostyrene

ACS Omega ◽  
2020 ◽  
Vol 5 (43) ◽  
pp. 27978-27989
Author(s):  
Isabel Méndez ◽  
Carlos Ferrer ◽  
Ricardo Rodríguez ◽  
Fernando J. Lahoz ◽  
Pilar García-Orduña ◽  
...  
Keyword(s):  
Enantioselective Alkylation

Practical Asymmetric Synthesis of Vicinal Diamines through the Catalytic Highly Enantioselective Alkylation of Glycine Amide Derivatives

2003 ◽  
Vol 115 (47) ◽  
pp. 6048-6050 ◽  
Author(s):  
Takashi Ooi ◽  
Daiki Sakai ◽  
Mifune Takeuchi ◽  
Eiji Tayama ◽  
Keiji Maruoka
Keyword(s):  
Asymmetric Synthesis ◽  
Amide Derivatives ◽  
Enantioselective Alkylation ◽  
Vicinal Diamines

Enantioselective alkylation of chiral enolates

1980 ◽  
Vol 21 (44) ◽  
pp. 4233-4236 ◽  
Author(s):  
D.A. Evans ◽  
J.M. Takacs
Keyword(s):  
Chiral Enolates ◽  
Enantioselective Alkylation

The First Catalytic Highly Enantioselective Alkylation of Ketimines — A Novel Approach to Optically Active Quaternary α-Amino Acids.

ChemInform ◽  
2004 ◽  
Vol 35 (16) ◽  
Author(s):  
Steen Saaby ◽  
Kimitaka Nakama ◽  
Mette Alstrup Lie ◽  
Rita G. Hazell ◽  
Karl Anker Joergensen
Keyword(s):  
Amino Acids ◽  
Optically Active ◽  
Novel Approach ◽  
Enantioselective Alkylation

Enantioselective Construction of Alkylated Stereogenic Centers

2013 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Phase Transfer ◽  
Enantioselective Hydrogenation ◽  
Gel Chromatography ◽  
Quaternary Centers ◽  
University Of Oxford ◽  
University Of Edinburgh ◽  
Enantioselective Alkylation ◽  
Silica Gel Chromatography ◽  
University Of Bristol ◽  
The University

Xiang-Ping Hu and Zhuo Zheng of the Dalian Institute of Chemical Physics developed (Organic Lett. 2009, 11, 3226; J. Org. Chem. 2009, 74, 9191) a family of Rh catalysts for the enantioselective hydrogenation of allylic phosphonates such as 1. Hon Wai Lam of the University of Edinburgh established (J. Am. Chem. Soc. 2009, 131, 10386) that an alkenyl heterocycle 3 could be reduced with high ee. The product 4 could be hydrolyzed to the carboxylic acid. Ken Tanaka of the Tokyo University of Agriculture and Technology showed (J. Am. Chem. Soc. 2009, 131, 12552) that an isopropenyl amide 6 could be hydroacylated with high ee. Gregory C. Fu of MIT observed (J. Am. Chem. Soc. 2009, 131, 14231) that nitromethane 9 could be added to the allenyl amide 8 to give 10, the product of γ-bond formation. Robert K. Boeckman Jr. of the University of Rochester devised (Organic Lett. 2009, 11, 4544) what appears to be a general protocol for the construction of alkylated ternary and quaternary centers: enantioselective hydroxymethylation of an aldehyde 11. In another approach to the construction of alkylated quaternary centers, Varinder K. Aggarwal of the University of Bristol demonstrated (Angew. Chem. Int. Ed. 2009, 48, 6289) that an enantiomerically enriched trifluoroborate salt 14 could be added to an aromatic aldehyde 15 with retention of absolute configuration. The salt 14 was prepared from the corresponding high ee secondary benzyl alcohol. Weinreb amides are versatile precursors to a variety of functional groups. Stephen G. Davies of the University of Oxford devised (Organic Lett. 2009, 11, 3254) a chiral Weinreb amide equivalent 17 that could be alkylated with high de. The minor diastereomer from the alkylation was readily separable by silica gel chromatography. Keiji Maruoka of Kyoto University established (Angew. Chem. Int. Ed. 2009, 48, 5014) that a chiral phase transfer catalyst was effective for the enantioselective alkylation of the alkynyl ester 19. Emmanuel Riguet of the Université de Reims Champagne-Ardenne developed (Tetrahedron Lett. 2009, 50, 4283) an improved catalyst for the enantioselective addition of malonate 22 to cyclohexenone 21.

C–N Ring Construction: The Harrity Synthesis of Quinolizidine (–)-217A

2015 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Phase Transfer ◽  
Iron Catalyst ◽  
Free Acid ◽  
Oxidative Cyclization ◽  
Colorado State University ◽  
University Of Tennessee ◽  
National University ◽  
Chiral Bronsted Acid ◽  
Enantioselective Alkylation ◽  
Seoul National University

David M. Jenkins of the University of Tennessee devised (J. Am. Chem. Soc. 2011, 133, 19342) an iron catalyst for the aziridination of an alkene 1 with an aryl azide 2. Yoshiji Takemoto of Kyoto University cyclized (Org. Lett. 2011, 13, 6374) the prochiral oxime derivative 4 to the azirine 5 in high ee. Organometallics added to 5 syn to the pendant ester. Hyeung-geun Park of Seoul National University used (Adv. Synth. Catal. 2011, 353, 3313) a chiral phase transfer catalyst to effect the enantioselective alkylation of 6 to 7. Yian Shi of Colorado State University showed (Org. Lett. 2011, 13, 6350) that a chiral Brønsted acid mediated the enantioselective cyclization of 8 to 9. Mattie S.M. Timmer of Victoria University of Wellington and Bridget L. Stocker of Malaghan Institute of Medical Research effected (J. Org. Chem. 2011, 76, 9611) the oxidative cyclization of 10 to 11. They also showed (Tetrahedron Lett. 2011, 52, 4803, not illustrated) that the same cyclization worked well to construct piperidine derivatives. Jose L. Vicario of the Universidad del País Vasco extended (Adv. Synth. Catal. 2011, 353, 3307) organocatalysis to the condensation of 12 with 13 to give the pyrrolidine 14. Jinxing Ye of the East China University of Science and Technology used (Adv. Synth. Catal. 2011, 353, 343) the same Hayashi catalyst to condense 15 with 16 to give 17. André B. Charette of the Université de Montreal expanded (Org. Lett. 2011, 13, 3830) 18, prepared by Petasis-Mannich coupling followed by ring-closing metathesis, to the piperidine 20. Marco Bella of the “Sapienza” University of Roma effected (Org. Lett. 2011, 13, 4546) enantioselective addition of 22 to the prochiral 21 to give 23. Ying-Chun Chen of Sichuan University and Chun-An Fan of Lanzhou University cyclized (Adv. Synth. Catal. 2011, 353, 2721) 24 to 25 in high ee. Andreas Schmid of TU Dortmund showed (Adv. Synth. Catal. 2011, 353, 2501) that ω-laurolactam hydrolases could be used to cyclize the ester 26, but not the free acid, to the macrolactam 27.

Sign in / Sign up

Export Citation Format

Share Document