By Thomas C. Nugent
This primary accomplished presentation of this sizzling and critical subject compiles the main up to date equipment for chiral amine synthesis. The foreign record of authors reads like a "Who's Who" of the topic, supplying a wide array of hugely useful info focused into the necessary and crucial methods.
Following an introductory bankruptcy dedicated to assisting readers fast verify which techniques to settle on for his or her research, this guide and prepared reference specializes in the exam of equipment which are trustworthy and concurrently effective for the synthesis of structurally various aliphatic and fragrant chiral amines. sleek equipment and purposes present in (pharmaceutical) also are covered.
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Extra info for Chiral Amine Synthesis Nugent
16), a reaction that has been primarily developed for catalytic asymmetric processes (see below). The hydrogenation of 1,3 enynes or 1,3 diynes in the presence of N sulﬁnyl iminoesters enables highly regio and stereoselective reductive coupling to afford diene and enyne containing a amino acid esters . 3) [64, 65]. 16 Rhodium(I) catalyzed arylboronic acid diastereoselective addition. 3 Diastereoselective addition to N sulfinyl ketimines. O N R1 S O t-Bu 1. Me3Al, Toluene t-Bu 2. 4 Catalytic Asymmetric Nucleophilic Addition to Achiral Imines j15 feature of this methodology is the ability to generate the starting imine as a major diastereomer.
50 mol%), Ligand S Acetone, 0 °C O S 1. 15 Preparation of tert butanesulfinamide. 2. 2 Diastereoselective addition to N tert butanesulfinyl imines derived from aldehydes. O O N R1 S tBu H Et2O/CH2Cl2 −48 °C 32 Entry 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 R H 2MgBr tBu S N O Br Mg HN R1 R2 R1 S R2 tBu HCl MeOH NH3Cl R1 R2 36 35 R1 Nucleophile Yield 35 (%) dr Et Et Et i Pr i Pr i Pr i Pr Ph Ph Ph Ph Bn Bn Bn Bn p MeOPh p MeOPh p MeOPh p MeOPh n Bu MeMgBr iPrMgBr PhMgBr MeMgBr EtMgBr PhMgBr VinylMgBr MeMgBr EtMgBr iPrMgBr VinylMgBr MeMgBr EtMgBr VinylMgBr PhMgBr EtMgBr PhCCLi TMSCCLi nBuCCLi PhCCLi 96 97 >98 97 >98 98 90 96 98 29 79 89 85 81 81 88 93 75 88 76 93 : 7 98 : 2 96 : 4 98 : 2 97 : 3 89 : 11 88 : 12 97 : 3 92 : 8 97 92 90 97 93 91 78 88 94 94 : 6 95 : 5 92 : 8 91 : 9 95 : 5 99 : 1 98 : 2 98 : 2 94 : 6 97 : 3 93 95 98 97 99 >98 Yield 36 (%) Grignard reagents to these imines proceeds very efﬁciently and generally with high diastereocontrol .
8). In addition, it is also possible to prepare N acyl and N carbamoyl imines via the following two step sequence . The treatment of an aldehyde with the corresponding amide in the presence of an arenesulﬁnic acid and formic acid in water generates the corresponding a acyl  or a carbamoyl sulfone . Subsequent basic treatment leads to N acyl or N carbamoyl imines. 8 Preparation of N acyl imines from nonenolizable aldehydes. 3 Chiral Auxiliary-Based Approaches The nucleophilic addition to imines bearing a chiral auxiliary is an extremely reliable, efﬁcient, and powerful strategy to generate a branched amines .