[Skip to Content](https://www.sigmaaldrich.com#main-content) [![MilliporeSigma](https://www.sigmaaldrich.com/static/logos/purple/millipore_sigma.svg)](https://www.sigmaaldrich.com/US/en) Products Cart0 USEN Products ProductsApplicationsServicesResourcesSupport [Login / Register](https://www.sigmaaldrich.com/oidc-sign-in) [Order Lookup](https://www.sigmaaldrich.com/US/en/order-lookup) [Quick Order](https://www.sigmaaldrich.com/US/en/quick-order) Cart0 [Home](https://www.sigmaaldrich.com/US/en)[Reaction Design & Optimization](https://www.sigmaaldrich.com/US/en/applications/chemistry-and-synthesis/reaction-design-and-optimization)Chiral Amines in Asymmetric Synthesis # Chiral Amines in Asymmetric Synthesis Chiral amines have found widespread application in asymmetric synthesis serving, for instance, as chiral bases in enantioselective deprotonation reactions1,2 or being valuable substances for resolving racemic mixtures of acids. Additionally, chiral amines are prevalent, essential parts of many drugs and drug candidates. ## α-Ethylbenzylamine Alexakis has reported on a practical solvent-free reductive amination reaction. In a one-pot synthesis, C2-symmetrical secondary amines could be obtained in high diastereoselectivities starting from (*R*)-α-ethylbenzylamine or (*S*)-α-ethylbenzylamine, respectively (__Figure 1__). ![α-Ethylbenzylamine](https://www.sigmaaldrich.com/content/dam/cms-commons/sigmaaldrich/marketing/global/images/technical-documents/articles/chemistry-and-synthesis/reaction-design-and-optimization/chiral-amines-schem-27.gif "α-Ethylbenzylamine") __Figure 1.__ α-Ethylbenzylamine These secondary amines also serve as valuable chiral building blocks for the synthesis of atropisomeric phosphoramidites used in highly enantioselective copper-catalyzed conjugate additions3,4 or in iridium-catalyzed allylic substitutions.5 ## 2-Amino-3-methylbutane Diazoxide BPDZ-44 was found to be a tissue selective ATP-sensitive potassium channel opener, resulting in inhibition of important physiological processes such as insulin release or muscle tone and contractility. The straightforward synthesis of BPDZ-44 used (*S*)-2-amino-3-methylbutane as a chiral building block in a key step (__Figure 2__).6 ![2-Amino-3-methylbutane](https://www.sigmaaldrich.com/content/dam/cms-commons/sigmaaldrich/marketing/global/images/technical-documents/articles/chemistry-and-synthesis/reaction-design-and-optimization/chiral-amines-scheme-27.gif "2-Amino-3-methylbutane") __Figure 2.__ 2-Amino-3-methylbutane ## Materials Sorry, an unexpected error has occurred Response not successful: Received status code 500 ### References 1\. Cox PJ, Simpkins NS. 1991. Asymmetric synthesis using homochiral lithium amide bases. Tetrahedron: Asymmetry. 2(1):1-26. [https://doi.org/10.1016/s0957-4166(00)82150-3](https://doi.org/10.1016/s0957-4166%2800%2982150-3) 2\. O'Brien P. 2002. Recent developments in chiral lithium amide base chemistry. Tetrahedron. 58(23):xi. [https://doi.org/10.1016/s0040-4020(02)00362-9](https://doi.org/10.1016/s0040-4020%2802%2900362-9) 3\. Alexakis A, Polet D, Rosset S, March S. 2004. Biphenol-Based Phosphoramidite Ligands for the Enantioselective Copper-Catalyzed Conjugate Addition of Diethylzinc. J. Org. Chem.. 69(17):5660-5667. [https://doi.org/10.1021/jo049359m](https://doi.org/10.1021/jo049359m) 4\. Alexakis A, Benhaim C. 2002. Eur.. J. Org. Chem.3221. 5\. Alexakis A, Polet D. 2004. Very Efficient Phosphoramidite Ligand for Asymmetric Iridium-Catalyzed Allylic Alkylation. Org. Lett.. 6(20):3529-3532. [https://doi.org/10.1021/ol048607y](https://doi.org/10.1021/ol048607y) 6\. Khelili S, de Tullio P, Lebrun P, Fillet M, Antoine M, Ouedraogo R, Dupont L, Fontaine J, Felekidis A, Leclerc G, et al. 1999. Preparation and pharmacological evaluation of the R - and S -enantiomers of 3-(2?-butylamino)-4 H - and 3-(3?-methyl-2?-butylamino)-4 H -pyrido\[4,3- e ]-1,2,4-thiadiazine 1,1-dioxide, two tissue selective ATP-sensitive potassium channel openers. Bioorganic & Medicinal Chemistry. 7(8):1513-1520. [https://doi.org/10.1016/s0968-0896(99)00082-6](https://doi.org/10.1016/s0968-0896%2899%2900082-6) __Related Articles__ - [ChiPros Chiral Amines](https://www.sigmaaldrich.com/US/en/technical-documents/technical-article/chemistry-and-synthesis/reaction-design-and-optimization/chipros-chiral-amines) - [Trialkylphosphine for MBH Reactions](https://www.sigmaaldrich.com/US/en/technical-documents/technical-article/chemistry-and-synthesis/cross-coupling/air-stable-trialkylphosphine) - [N-Heterocyclic Carbene Ligands](https://www.sigmaaldrich.com/US/en/technical-documents/technical-article/chemistry-and-synthesis/cross-coupling/carbene-ligands) - [CBS Catalysts](https://www.sigmaaldrich.com/US/en/technical-documents/technical-article/chemistry-and-synthesis/cross-coupling/cbs-catalysts) - [KitAlysis™ High-Throughput Screening Platform](https://www.sigmaaldrich.com/US/en/technical-documents/technical-article/chemistry-and-synthesis/cross-coupling/kitalysis) - [Scale-Up Guide: Suzuki-Miyaura Cross-Coupling Reaction](https://www.sigmaaldrich.com/US/en/technical-documents/technical-article/chemistry-and-synthesis/cross-coupling/s-m-kitalysis-scale-up) - [TPGS-750-M: Second-Generation Amphiphile for Organometallic Chemistry in Water at Room Temperature](https://www.sigmaaldrich.com/US/en/technical-documents/technical-article/chemistry-and-synthesis/cross-coupling/tpgs-750-m) - [Fluoroalkylation: Expansion of Togni Reagents](https://www.sigmaaldrich.com/US/en/technical-documents/technical-article/chemistry-and-synthesis/fluorination/fluoralkylation) __Related Product Categories__ - [Chiral Catalysts & Ligands](https://www.sigmaaldrich.com/US/en/products/chemistry-and-biochemicals/catalysts/chiral-catalysts-and-ligands) - [Environmental Accounting Supplier Toolkit](https://www.sigmaaldrich.com/US/en/life-science/ssbi/sustainability-toolkits/environmental-accounting-supplier-toolkit) - [Renewable Electricity Toolkit](https://www.sigmaaldrich.com/US/en/life-science/ssbi/sustainability-toolkits/renewable-electricity-toolkit) - [Crown Ethers and Cryptands for Advanced Applications](https://www.sigmaaldrich.com/US/en/technical-documents/product-supporting/crown-ethers-cryptands-advanced-applications) - [Purification of Extracellular Vesicles with Eshmuno® Q Resin and Natrix® Q Membrane](https://www.sigmaaldrich.com/US/en/technical-documents/product-supporting/membrane-chromatography/purification-extracellular-vesicles) - [Sterilizing filters for final sterile filtration](https://www.sigmaaldrich.com/US/en/technical-documents/product-supporting/pharma-and-biopharma-manufacturing/final-sterile-filtration-and-filling/sterilizing-grade-membrane-filters) - [Single-use assemblies for final sterile filtration](https://www.sigmaaldrich.com/US/en/technical-documents/product-supporting/pharma-and-biopharma-manufacturing/mobius-single-use-assemblies/single-use-filtration-assemblies) - [Membrane Prefilters Improve Sterilizing Filter Capacity and Process Economics in Bioprocessing](https://www.sigmaaldrich.com/US/en/technical-documents/product-supporting/prefilters-bioburden-control/membrane-prefiltration-improves-sterilizing-filter-capacity-and-process-economics) Top __Sign In To Continue__ To continue reading please sign in or create an account. Sign In__Don't Have An Account?__Register Support[Customer Support](https://www.sigmaaldrich.com/US/en/support/customer-support)[Contact Us](https://www.sigmaaldrich.com/US/en/collections/offices)[FAQ](https://maestro.my.site.com/knowledgeportal/s/)[Safety Data Sheets (SDS)](https://www.sigmaaldrich.com/US/en/documents-search?tab=sds)[Certificates (COA/COO)](https://www.sigmaaldrich.com/US/en/documents-search?tab=coa)[Quality & Regulatory](https://www.sigmaaldrich.com/US/en/life-science/quality-and-regulatory-management)[Calculators & Apps](https://www.sigmaaldrich.com/US/en/support/calculators-and-apps)[Webinars](https://www.sigmaaldrich.com/US/en/collections/webinars) Orders[Order Lookup](https://www.sigmaaldrich.com/US/en/order-lookup)[Quick Order](https://www.sigmaaldrich.com/US/en/quick-order)[Custom Products](https://www.sigmaaldrich.com/US/en/services/custom-products)[eCommerce Solutions](https://www.sigmaaldrich.com/US/en/life-science/ecommerce/ecommerce-solutions) Company[About Us](https://www.sigmaaldrich.com/US/en/life-science/about-us)[Responsibility](https://www.sigmaaldrich.com/US/en/life-science/ssbi)[Events](https://www.sigmaaldrich.com/US/en/collections/events)[Press Releases](https://www.sigmaaldrich.com/US/en/collections/press)[Programs](https://www.sigmaaldrich.com/US/en/life-science/partnership-programs)[Careers](https://careers.merckgroup.com/global/en)[Offices](https://www.sigmaaldrich.com/US/en/collections/offices) Social Media [![LinkedIn icon](https://www.sigmaaldrich.com/content/dam/cms-commons/sigmaaldrich/marketing/global/images/icons/linkedin.svg)](https://www.linkedin.com/company/merck-life-science) [![X icon](https://www.sigmaaldrich.com/content/dam/cms-commons/sigmaaldrich/marketing/global/images/icons/x-icon.svg)](https://x.com/Merck_lifesci) [![Facebook Icon](https://www.sigmaaldrich.com/content/dam/cms-commons/sigmaaldrich/marketing/global/images/icons/facebook.svg)](https://www.facebook.com/Merck.lifescience) [![Instagram Icon](https://www.sigmaaldrich.com/content/dam/cms-commons/sigmaaldrich/marketing/global/images/icons/instagram.svg)](https://www.instagram.com/mercklifescience/) [![YouTube Icon](https://www.sigmaaldrich.com/content/dam/cms-commons/sigmaaldrich/marketing/global/images/icons/youtube.svg)](https://www.youtube.com/@MerckLifeScience/featured) MilliporeSigma __Research. Development. Production.__ We are a leading supplier to the global Life Science industry with solutions and services for research, biotechnology development and production, and pharmaceutical drug therapy development and production. [![Vibrant M string](https://www.sigmaaldrich.com/content/dam/cms-commons/sigmaaldrich/marketing/global/images/icons/vibrant-m-string-1-rrvcrp.svg)](https://www.sigmaaldrich.com/US/en) [Sigma-Aldrich® Solutions](https://www.sigmaaldrich.com/US/en/life-science/sigma-aldrich)[BioReliance® Solutions](https://www.sigmaaldrich.com/US/en/life-science/bioreliance)[Millipore® Solutions](https://www.sigmaaldrich.com/US/en/life-science/millipore)[SAFC® Solutions](https://www.sigmaaldrich.com/US/en/life-science/safc)[Milli-Q® Solutions](https://www.sigmaaldrich.com/US/en/life-science/milliq)[Supelco® Solutions](https://www.sigmaaldrich.com/US/en/life-science/supelco) © 2026 Merck KGaA, Darmstadt, Germany and/or its affiliates. All Rights Reserved, including Text and Data Mining for AI training and similar technologies. Reproduction of any materials from the site is strictly forbidden without permission. [Site Use Terms](https://www.sigmaaldrich.com/US/en/life-science/legal/site-use-terms)|[Privacy Policy](https://www.sigmaaldrich.com/US/en/life-science/legal/privacy-statement)|[General Terms and Conditions of Sale](https://www.sigmaaldrich.com/US/en/life-science/legal/terms-and-conditions)|[Copyright Consent](https://www.sigmaaldrich.com/US/en/life-science/legal/copyright-consent) |[Site Map](https://www.sigmaaldrich.com/US/en/site-map) An unknown error has occured.