New PDF release: Dynamic Stereochemistry of Chiral Compounds: Principles and

By Christian Wolf

ISBN-10: 0854042466

ISBN-13: 9780854042463

This e-book offers an summary of primary techniques of uneven synthesis highlighting the importance of stereochemical and stereodynamic response keep an eye on. subject matters contain kinetic solution (KR), dynamic kinetic solution (DKR), dynamic kinetic uneven transformation (DYKAT), and dynamic thermodynamic solution (DTR). In-depth discussions of uneven synthesis with chiral organolithium compounds, atropisomeric biaryl synthesis, self-regeneration of stereogenicity (SRS), chiral amplification with chiral relays and different general concepts also are supplied. specific emphasis is given to selective creation, interconversion and translocation of critical, axial, planar, and helical chirality. a scientific insurance of stereochemical ideas and stereodynamic homes of chiral compounds publications the reader in the course of the e-book and establishes a conceptual linkage to uneven synthesis, molecular units that resemble the constitution and stereomutations of propellers, bevel gears, switches and vehicles, and topologically chiral assemblies comparable to catenanes and rotaxanes. Racemization and diastereomerization reactions of various chiral compounds are mentioned in addition to the foundations, scope and compatibility of accepted analytical suggestions. info of analytical tools are supplied and mentioned in addition to themes in relation to the layout of attention-grabbing topologically chiral assemblies and molecular technomimetic units within the context of dynamic stereochemistry. techniques and up to date advancements that handle vital man made demanding situations are provided and highlighted with 1000's of examples, purposes and targeted mechanisms. This remarkable booklet contains: - greater than 550 figures, schemes and tables illustrating mechanisms of various uneven reactions and stereomutations of chiral compounds - Technical drawings illustrating the conceptual linkage among macroscopic units corresponding to turnstiles, ratchets, brakes, bevel gears or knots and molecular analogs - greater than 3000 references to inspire additional studying and facilitate extra literature learn - A accomplished word list with stereochemical definitions and phrases which facilitate figuring out and make stronger studying This e-book may be of specific curiosity to undergraduates, graduates and pros operating and discovering within the fields of natural man made chemistry and analytical chemistry.

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Extra info for Dynamic Stereochemistry of Chiral Compounds: Principles and Applications

Sample text

Since the contribution from the less stable cyclohexanone conformer having the tert-butyl group in the axial position is negligible, the prediction of diastereoselective reactions of 4-tert-butylcyclohexanone is simplified and requires stereochemical analysis of only a single conformer. Most nucleophiles including Grignard and organolithium reagents approach the carbonyl group at an angle close to 109 1 (Bu¨rgi–Dunitz trajectory) from the site opposite to the bulky tert-butyl group. Reetz and Stanchev obtained the axial carbinol via organiron(II)-mediated diastereofacial addition of butylmagnesium chloride in 76% de.

Tauber J. J. Res. Nat. Bur. Stand. Sect. A. 1963, 67, 591-599. 7. ; Vo¨gtle, F. Chem. Eur. J. 2000, 6, 1674-1682. 8. ; Gerlach, H. Helv. Chim. Acta 1964, 47, 2288-2294. 9. ; Owtschinnikow, J. ; Prelog, V. Helv. Chim. Acta 1964, 47, 2294-2302. 10. Mislow, K. Chimia 1986, 40, 395-402. 11. ; Goodman, M. Acc. Chem. Res. 1992, 25, 266-272. 12. Eliel, E. L; Wilen, S. H. Stereochemistry of Organic Compounds, Wiley, New York, 1994, pp. 1176-1181. 13. ; Ko¨nig, W. ; Roussel, C. Chirality 1995, 7, 610-611.

Application of the two conventions to axially chiral compounds reveals that descriptors Ra and M, as well as Sa and P, correspond to each other. In the case of planar chirality, the descriptors Rp and P, and Sp and M, respectively, are synonymous. ii The use of suffixes a and p to indicate axial and planar chirality is optional. 10 achiral achiral achiral achiral chiral Achiral (a) and chiral (b) catenanes devoid of classical elements of chirality. In addition to classical or Euclidian elements of chirality, introduction of directionality to mechanically interlocked molecules can generate so-called topological chirality.

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