scholarly journals Asymmetric synthesis using chiral acetals: Highly diastereoselective nucleophilic addition of Grignard reagents to chiral 1-oxo-.BETA.-tetralone 1-acetals.

1989 ◽  
Vol 37 (6) ◽  
pp. 1488-1492 ◽  
Author(s):  
Hiromichi FUJIOKA ◽  
Hiroshi KONDO ◽  
Hirokazu ANNOURA ◽  
Hirofumi YAMAMOTO ◽  
Tomoko KO ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Nucleophilic Addition ◽  
Grignard Reagents

Bifunctional Squaramide Catalyzed Asymmetric Synthesis of Chiral α-Mercaptosilanes

2021 ◽  
Author(s):  
Ye Zhang ◽  
Jingcheng Guo ◽  
Jinna Han ◽  
Xiangui Zhou ◽  
Wei Cao ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Carbonyl Compounds ◽  
Nucleophilic Addition

Bifunctional squaramide-catalyzed nucleophilic addition of thiophenols to easily available β-silyl α,β-unsaturated carbonyl compounds has been successfully developed. A structurally diverse set of chiral α-mercaptosilanes was efficiently prepared in good to...

Asymmetric Synthesis of Homoallylamines by Nucleophilic Addition of Chirally Modified Allylboron Reagent to N-Borylimines

Synlett ◽  
1999 ◽  
Vol 1999 (12) ◽  
pp. 1987-1989 ◽  
Author(s):  
Shinichi Itsuno ◽  
Ayako Yokoi ◽  
Shizue Kuroda
Keyword(s):  
Asymmetric Synthesis ◽  
Nucleophilic Addition

scholarly journals Iron-Catalyzed C(sp2)–C(sp3) Cross-Coupling of Aryl Chlorobenzoates with Alkyl Grignard Reagents

Molecules ◽  
2020 ◽  
Vol 25 (1) ◽  
pp. 230 ◽  
Author(s):  
Elwira Bisz ◽  
Michal Szostak
Keyword(s):  
Organic Synthesis ◽  
Nucleophilic Addition ◽  
Functional Group ◽  
High Selectivity ◽  
Cross Coupling ◽  
Environmentally Benign ◽  
Grignard Reagents ◽  
High Importance ◽  
Iron Salts ◽  
The Cross

Aryl benzoates are compounds of high importance in organic synthesis. Herein, we report the iron-catalyzed C(sp2)–C(sp3) Kumada cross-coupling of aryl chlorobenzoates with alkyl Grignard reagents. The method is characterized by the use of environmentally benign and sustainable iron salts for cross-coupling in the catalytic system, employing benign urea ligands in the place of reprotoxic NMP (NMP = N-methyl-2-pyrrolidone). It is notable that high selectivity for the cross-coupling is achieved in the presence of hydrolytically-labile and prone to nucleophilic addition phenolic ester C(acyl)–O bonds. The reaction provides access to alkyl-functionalized aryl benzoates. The examination of various O-coordinating ligands demonstrates the high activity of urea ligands in promoting the cross-coupling versus nucleophilic addition to the ester C(acyl)–O bond. The method showcases the functional group tolerance of iron-catalyzed Kumada cross-couplings.

scholarly journals Applications of tert-butanesulfinamide in the asymmetric synthesis of amines

2003 ◽  
Vol 75 (1) ◽  
pp. 39-46 ◽  
Author(s):  
J. A. Ellman
Keyword(s):  
Amino Acids ◽  
Asymmetric Synthesis ◽  
Nucleophilic Addition ◽  
Amino Alcohols ◽  
Wide Range ◽  
Aldehydes And Ketones ◽  
Directing Group ◽  
High Yields ◽  
Direct Condensation

tert-Butanesulfinamide is prepared using catalytic enantioselective methods in two steps from the extremely inexpensive oil waste by-product, tert-butyl disulfide. Direct condensation of tert-butanesulfinamide with aldehydes and ketones provides tert-butanesulfinyl imines in uniformly high yields. The tert-butanesulfinyl group activates the imines for the addition of many different classes of nucleophiles, serves as a powerful chiral directing group, and after nucleophilic addition is readily cleaved by treatment with acid. A wide range of highly enantioenriched amines, including α-branched and α,α-dibranched amines, α- and β-amino acids, 1,2 and 1,3-amino alcohols and α-trifluoromethyl amines are efficiently synthesized using this methodology.

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