Abstract
The basics of stereoselective reactions and reaction stereochemistry—the relation of stereoselectivity to the topology of tetrahedral and planar units in organic molecules—are discussed. The kinetic control of enantioselective reactions and characteristics of enantioselective and diastereoslective reactions is presented. Asymmetric syntheses are exemplified by the hydrogenation of C=O and C=NR bonds in prochiral substrates catalyzed by organometallic complexes with chiral phosphine ligands. The mechanism of asymmetric alkylation of stabilized carbanions in specifically designed chiral substrates and the practicability of this method in the preparation of optically pure α-alkyl carboxylic acids are discussed. The synthetic approach to chiral auxiliaries and importance of recycling are presented.
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References
Nogradi M (1981) Stereochemistry, basic concepts and applications. Akademia Kiado, Budapest
Eliel E, Wilen SH (1994) Stereochemistry of organic compounds. Wiley Interscience, New York
Juaristi E (1991) Introduction to stereochemistry and conformational analysis. Wiley, New York
Anslyn EV, Dougherty DA (2005) Modern physical organic chemistry, chapter 6, Stereochemistry. University Science Books, Herndon, VA
Solodar J (1975) Chem Tech 421–423
Hasaguchi S, Kanehira K, Kumada M (1981) Tetrahedron Lett 22:4417–4420
Landis CR, Halpern J (1987) J Am Chem Soc 109:1746–1754
Hashiguchi S, Fujii A, Takehara J, Ikariya T, Noyori R (1995) J Am Chem Soc 117:7562–7563
Fujii A, Hashiguchi S, Uematsu N, Ikaraya T, Noyori R (1996) J Am Chem Soc 118:2521–2522
Burk MJ (1991) J Am Chem Soc 113:8518–8519
Shultz CS, Kirska SW (2007) Acc Chem Res 40:1320–1326
Hsiao Y, Riviera NR, Rosner T, Kirska SW, Njolito E, Wang F, Sun Y, Armstrong III JD, E. Grabowski EJJ, Tillyer RD, Spindler F, Malan C (2004) J Am Chem Soc 126:9918–9919
Noyori R, Kitamura M, Ohkuma T (2004) Proc Nac Acad Sci USA 101:5356–5362
Davies SG, Fletcher AM, Lv L, Roberts PM, Thomson JE (2012) Tetrahedron Lett 52:3052–3055
Lutomski KA, Mayers AI (1984) Asymmetric synthesis (Morrison D, ed), vol 3. Academic Press, New York, pp 231–274
Meyers AI, Snyder ES, Ackerman JJH (1978) J Am Chem Soc 100:8186–8189
Procter G (1996) Asymmetric synthesis. Oxford Science Publications, Oxford, pp 41–68
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Šunjić, V., Petrović Peroković, V. (2016). Stereoisomers and Stereoselective Reactions—“Departure into Third Dimension”. In: Organic Chemistry from Retrosynthesis to Asymmetric Synthesis. Springer, Cham. https://doi.org/10.1007/978-3-319-29926-6_3
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DOI: https://doi.org/10.1007/978-3-319-29926-6_3
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