By Thomas C. Nugent
This primary accomplished presentation of this sizzling and demanding subject compiles the main updated 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 sensible details centred into the worthy and crucial methods.Following an introductory bankruptcy dedicated to assisting readers fast be sure which ideas to settle on for his or her research, this instruction manual and prepared reference makes a speciality of the exam of tools which are trustworthy and at the same time effective for the synthesis of structurally various aliphatic and fragrant chiral amines. glossy tools and purposes present in (pharmaceutical) also are coated.
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Extra resources for Chiral Amine Synthesis: Methods, Developments and Applications
One of the most general methods compatible with both nonenolizable and enolizable aldehydes involves the initial formation of the sulﬁnic acid adduct of the imine from an aldehyde and p-toluenesulﬁnic acid formed in situ from formic acid and sodium benzene sulﬁnate O R1 O R1 H A TsN(Cl)Na (2 equiv) Te Toluene B TsNH2, Si(OEt)4 C NTs 1. p-TolS(O)NH2 O R1 H H 2. 5 Methods for the preparation of N-sulfonyl imines. 2 Overview of the Methods for the Preparation of Imines (method D) . A subsequent base treatment generates the N-tosyl imines.
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 . 2). Both strategies are complementary and will be reviewed separately in the following two sections. 2 Complementary approaches for the incorporation of a chiral auxiliary. 3) . 9) [33b]. Imine formation, followed by Grignard addition, leads to amine 7 in 86% yield as a single diastereomer. Acid hydrolysis affords the a-amino aldehyde 9 in good yields.
2 Rhodium Phosphine-Catalyzed Arylation of Imines The asymmetric rhodium-catalyzed arylation of imines is among the most efﬁcient methods for the preparation of a-aryl chiral amines. 31 Rhodium-catalyzed arylation of N-arenesulfonyl imines. 31). Both reactions presumably proceed via the formation of an arylrhodium species that is complexed to the chiral ligand. Several aryl sulfonyl groups were screened, and the p-nitro derivatives gave not only the highest ees when (R)-ArÃ-MOP was used as the ligand but also the highest yields when 4 equiv of various arylstannanes were employed.
Chiral Amine Synthesis: Methods, Developments and Applications by Thomas C. Nugent