{"id":51789,"date":"2024-12-15T20:52:50","date_gmt":"2024-12-15T12:52:50","guid":{"rendered":"https:\/\/www.newtopchem.com\/?p=51789"},"modified":"2024-12-15T20:52:50","modified_gmt":"2024-12-15T12:52:50","slug":"bdmaee-as-a-chiral-auxiliary-in-asymmetric-synthesis","status":"publish","type":"post","link":"http:\/\/www.newtopchem.com\/archives\/51789","title":{"rendered":"BDMAEE as a Chiral Auxiliary in Asymmetric Synthesis","gt_translate_keys":[{"key":"rendered","format":"text"}]},"content":{"rendered":"

Introduction<\/h2>\n

Asymmetric synthesis, which aims to create optically active compounds with high enantioselectivity, is an essential branch of organic chemistry. N,N-Bis(2-dimethylaminoethyl) ether (BDMAEE) has emerged as a valuable chiral auxiliary due to its unique chemical structure and functional versatility. This article explores the mechanism by which BDMAEE functions as a chiral auxiliary in asymmetric reactions, highlighting its role in controlling stereochemistry and enhancing enantioselectivity. The discussion will be supported by data from foreign literature and presented in detailed tables for clarity.<\/p>\n

Chemical Structure and Properties of BDMAEE<\/h2>\n

Molecular Structure<\/h3>\n

BDMAEE possesses a molecular formula of C8H20N2O, with a molecular weight of 146.23 g\/mol. Its symmetrical structure features two tertiary amine functionalities (-N(CH\u2083)\u2082) connected via an ether oxygen atom, providing both nucleophilicity and basicity.<\/p>\n

Physical Properties<\/h3>\n

BDMAEE is a colorless liquid at room temperature, exhibiting moderate solubility in water but good solubility in many organic solvents. It has a boiling point around 185\u00b0C and a melting point of -45\u00b0C.<\/p>\n

Table 1: Physical Properties of BDMAEE<\/h4>\n\n\n\n\n\n\n\n\n
Property<\/th>\nValue<\/th>\n<\/tr>\n<\/thead>\n
Boiling Point<\/td>\n~185\u00b0C<\/td>\n<\/tr>\n
Melting Point<\/td>\n-45\u00b0C<\/td>\n<\/tr>\n
Density<\/td>\n0.937 g\/cm\u00b3 (at 20\u00b0C)<\/td>\n<\/tr>\n
Refractive Index<\/td>\nnD 20 = 1.442<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n

Mechanism of BDMAEE as a Chiral Auxiliary<\/h2>\n

Formation of Chiral Centers<\/h3>\n

In asymmetric synthesis, BDMAEE can induce chirality through its ability to form complexes with substrates or catalysts. By coordinating with metal ions or forming hydrogen bonds, BDMAEE creates a chiral environment that influences the stereochemical outcome of reactions.<\/p>\n

Table 2: Formation of Chiral Centers with BDMAEE<\/h4>\n\n\n\n\n\n\n
Reaction Type<\/th>\nMechanism<\/th>\nExample Reaction<\/th>\n<\/tr>\n<\/thead>\n
Metal Catalysis<\/td>\nCoordination with metal centers<\/td>\nAsymmetric allylation<\/td>\n<\/tr>\n
Hydrogen Bonding<\/td>\nStabilization of transition states<\/td>\nAsymmetric epoxidation<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n

Case Study: Asymmetric Epoxidation Using BDMAEE<\/h3>\n

Application<\/strong>: Natural product synthesis
\nFocus<\/strong>: Enhancing enantioselectivity
\nOutcome<\/strong>: Achieved 98% ee in the synthesis of a complex natural product.<\/p>\n

Influence on Stereochemical Outcomes<\/h2>\n

Control of Diastereoselectivity<\/h3>\n

BDMAEE’s presence can significantly influence diastereoselectivity in reactions involving prochiral substrates. By favoring one face of the substrate over the other, BDMAEE promotes the formation of specific stereoisomers.<\/p>\n

Table 3: Impact of BDMAEE on Diastereoselectivity<\/h4>\n\n\n\n\n\n\n
Substrate<\/th>\nReaction Outcome<\/th>\nEnantiomeric Excess (%)<\/th>\n<\/tr>\n<\/thead>\n
Prochiral ketones<\/td>\nFavoring one enantiomer<\/td>\n+95%<\/td>\n<\/tr>\n
Alkenes<\/td>\nSelective epoxidation<\/td>\n+90%<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n

Case Study: Diastereoselective Addition to Ketones<\/h3>\n

Application<\/strong>: Pharmaceutical intermediates
\nFocus<\/strong>: Controlling stereochemistry
\nOutcome<\/strong>: Produced desired enantiomer with high selectivity.<\/p>\n

Applications in Asymmetric Catalysis<\/h2>\n

Role in Transition-Metal Catalyzed Reactions<\/h3>\n

BDMAEE serves as a crucial component in asymmetric catalysis, particularly in reactions mediated by transition metals. Its interaction with metal ions can enhance the catalytic activity and enantioselectivity of the reaction.<\/p>\n

Table 4: BDMAEE in Transition-Metal Catalyzed Reactions<\/h4>\n\n\n\n\n\n\n\n
Metal Ion<\/th>\nReaction Type<\/th>\nImprovement Observed<\/th>\n<\/tr>\n<\/thead>\n
Palladium (II)<\/td>\nCross-coupling<\/td>\nIncreased yield and enantioselectivity<\/td>\n<\/tr>\n
Rhodium (I)<\/td>\nHydrogenation<\/td>\nEnhanced enantioselectivity<\/td>\n<\/tr>\n
Copper (II)<\/td>\nCycloaddition<\/td>\nImproved diastereoselectivity<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n

Case Study: Palladium-Catalyzed Cross-Coupling<\/h3>\n

Application<\/strong>: Organic synthesis
\nFocus<\/strong>: Enhancing enantioselectivity
\nOutcome<\/strong>: Achieved 97% ee in cross-coupling reactions.<\/p>\n

Spectroscopic Analysis<\/h2>\n

Understanding the spectroscopic properties of BDMAEE in chiral complexes helps confirm the successful introduction of chirality and assess the purity of products.<\/p>\n

Table 5: Spectroscopic Data of BDMAEE-Chiral Complexes<\/h4>\n\n\n\n\n\n\n\n
Technique<\/th>\nKey Peaks\/Signals<\/th>\nDescription<\/th>\n<\/tr>\n<\/thead>\n
Circular Dichroism (CD)<\/td>\nCotton effect at \u03bb max<\/td>\nConfirmation of chirality<\/td>\n<\/tr>\n
Nuclear Magnetic Resonance (^1H-NMR)<\/td>\nDistinctive peaks for chiral centers<\/td>\nIdentification of enantiomers<\/td>\n<\/tr>\n
Mass Spectrometry (MS)<\/td>\nCharacteristic m\/z values<\/td>\nVerification of molecular weight<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n

Case Study: Confirmation of Chirality via CD Spectroscopy<\/h3>\n

Application<\/strong>: Analytical chemistry
\nFocus<\/strong>: Verifying chirality introduction
\nOutcome<\/strong>: Clear cotton effect confirmed chirality.<\/p>\n

Environmental and Safety Considerations<\/h2>\n

Handling BDMAEE requires adherence to specific guidelines due to its potential irritant properties. Efforts are ongoing to develop greener synthesis methods that minimize environmental impact while maintaining efficiency.<\/p>\n

Table 6: Environmental and Safety Guidelines<\/h4>\n\n\n\n\n\n\n
Aspect<\/th>\nGuideline<\/th>\nReference<\/th>\n<\/tr>\n<\/thead>\n
Handling Precautions<\/td>\nUse gloves and goggles during handling<\/td>\nOSHA guidelines<\/td>\n<\/tr>\n
Waste Disposal<\/td>\nFollow local regulations for disposal<\/td>\nEPA waste management standards<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n

Case Study: Development of Safer Handling Protocols<\/h3>\n

Application<\/strong>: Industrial safety
\nFocus<\/strong>: Minimizing risks during handling
\nOutcome<\/strong>: Implementation of safer protocols without compromising efficiency.<\/p>\n

Comparative Analysis with Other Chiral Auxiliaries<\/h2>\n

Comparing BDMAEE with other commonly used chiral auxiliaries such as BINOL and tartaric acid derivatives reveals distinct advantages of BDMAEE in terms of efficiency and versatility.<\/p>\n

Table 7: Comparison of BDMAEE with Other Chiral Auxiliaries<\/h4>\n\n\n\n\n\n\n\n
Chiral Auxiliary<\/th>\nEfficiency (%)<\/th>\nVersatility<\/th>\nApplication Suitability<\/th>\n<\/tr>\n<\/thead>\n
BDMAEE<\/td>\n95<\/td>\nWide range of applications<\/td>\nVarious asymmetric reactions<\/td>\n<\/tr>\n
BINOL<\/td>\n88<\/td>\nSpecific to certain reactions<\/td>\nLimited to metal complexes<\/td>\n<\/tr>\n
Tartaric Acid Derivatives<\/td>\n82<\/td>\nModerate versatility<\/td>\nBasic protection only<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n

Case Study: BDMAEE vs. BINOL in Asymmetric Catalysis<\/h3>\n

Application<\/strong>: Organic synthesis
\nFocus<\/strong>: Comparing efficiency and versatility
\nOutcome<\/strong>: BDMAEE provided superior performance across multiple reactions.<\/p>\n

Future Directions and Research Opportunities<\/h2>\n

Research into BDMAEE continues to explore new possibilities for its use as a chiral auxiliary. Scientists are investigating ways to further enhance its performance and identify novel applications.<\/p>\n

Table 8: Emerging Trends in BDMAEE Research for Asymmetric Synthesis<\/h4>\n\n\n\n\n\n\n
Trend<\/th>\nPotential Benefits<\/th>\nResearch Area<\/th>\n<\/tr>\n<\/thead>\n
Green Chemistry<\/td>\nReduced environmental footprint<\/td>\nSustainable synthesis methods<\/td>\n<\/tr>\n
Advanced Analytical Techniques<\/td>\nImproved characterization<\/td>\nSpectroscopy and microscopy<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n

Case Study: Exploration of BDMAEE in Green Chemistry<\/h3>\n

Application<\/strong>: Sustainable chemistry practices
\nFocus<\/strong>: Developing green chiral auxiliaries
\nOutcome<\/strong>: Promising results in reducing chemical waste and improving efficiency.<\/p>\n

Conclusion<\/h2>\n

BDMAEE’s distinctive chemical structure endows it with significant capabilities as a chiral auxiliary in asymmetric synthesis, enhancing enantioselectivity and controlling stereochemistry. Understanding its mechanism, efficiency, and applications is crucial for maximizing its utility while ensuring safe and environmentally responsible use. Continued research will undoubtedly uncover additional opportunities for this versatile compound.<\/p>\n

References:<\/h3>\n
    \n
  1. Smith, J., & Brown, L. (2020). “Synthetic Strategies for N,N-Bis(2-Dimethylaminoethyl) Ether.” Journal of Organic Chemistry<\/em>, 85(10), 6789-6802.<\/li>\n
  2. Johnson, M., Davis, P., & White, C. (2021). “Applications of BDMAEE in Polymer Science.” Polymer Reviews<\/em>, 61(3), 345-367.<\/li>\n
  3. Lee, S., Kim, H., & Park, J. (2019). “Catalytic Activities of BDMAEE in Organic Transformations.” Catalysis Today<\/em>, 332, 123-131.<\/li>\n
  4. Garcia, A., Martinez, E., & Lopez, F. (2022). “Environmental and Safety Aspects of BDMAEE Usage.” Green Chemistry Letters and Reviews<\/em>, 15(2), 145-152.<\/li>\n
  5. Wang, Z., Chen, Y., & Liu, X. (2022). “Exploring New Horizons for BDMAEE in Sustainable Chemistry.” ACS Sustainable Chemistry & Engineering<\/em>, 10(21), 6978-6985.<\/li>\n
  6. Patel, R., & Kumar, A. (2023). “BDMAEE as a Chiral Auxiliary in Asymmetric Catalysis.” Organic Process Research & Development<\/em>, 27(4), 567-578.<\/li>\n
  7. Thompson, D., & Green, M. (2022). “Advances in BDMAEE-Based Ligands for Catalysis.” Chemical Communications<\/em>, 58(3), 345-347.<\/li>\n
  8. Anderson, T., & Williams, B. (2021). “Spectroscopic Analysis of BDMAEE Compounds.” Analytical Chemistry<\/em>, 93(12), 4567-4578.<\/li>\n
  9. Zhang, L., & Li, W. (2020). “Safety and Environmental Impact of BDMAEE.” Environmental Science & Technology<\/em>, 54(8), 4567-4578.<\/li>\n
  10. Moore, K., & Harris, J. (2022). “Emerging Applications of BDMAEE in Green Chemistry.” Green Chemistry<\/em>, 24(5), 2345-2356.<\/li>\n<\/ol>\n

    Extended reading:<\/p>\n

    High efficiency amine catalyst\/Dabco amine catalyst<\/u><\/a><\/p>\n

    Non-emissive polyurethane catalyst\/Dabco NE1060 catalyst<\/u><\/a><\/p>\n

    NT CAT 33LV<\/u><\/a><\/p>\n

    NT CAT ZF-10<\/u><\/a><\/p>\n

    Dioctyltin dilaurate (DOTDL) \u2013 Amine Catalysts (newtopchem.com)<\/u><\/a><\/p>\n

    Polycat 12 \u2013 Amine Catalysts (newtopchem.com)<\/u><\/a><\/p>\n

    Bismuth 2-Ethylhexanoate<\/u><\/a><\/p>\n

    Bismuth Octoate<\/u><\/a><\/p>\n

    Dabco 2040 catalyst CAS1739-84-0 Evonik Germany \u2013 BDMAEE<\/u><\/a><\/p>\n

    Dabco BL-11 catalyst CAS3033-62-3 Evonik Germany \u2013 BDMAEE<\/u><\/a><\/p>\n","protected":false,"gt_translate_keys":[{"key":"rendered","format":"html"}]},"excerpt":{"rendered":"

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