By Christian Wolf
ISBN-10: 0854042466
ISBN-13: 9780854042463
ISBN-10: 1615833579
ISBN-13: 9781615833573
ISBN-10: 1847558097
ISBN-13: 9781847558091
This publication offers an summary of primary thoughts of uneven synthesis highlighting the importance of stereochemical and stereodynamic response keep an eye on. subject matters contain kinetic answer (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 usual thoughts 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 rules and stereodynamic homes of chiral compounds courses the reader throughout 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 equivalent to catenanes and rotaxanes. Racemization and diastereomerization reactions of various chiral compounds are mentioned in addition to the rules, scope and compatibility of ordinary analytical innovations. info of analytical tools are supplied and mentioned in addition to subject matters on the subject of the layout of attention-grabbing topologically chiral assemblies and molecular technomimetic units within the context of dynamic stereochemistry. concepts and up to date advancements that deal with very important man made demanding situations are offered and highlighted with enormous quantities of examples, purposes and particular mechanisms. This unparalleled e-book comprises: - greater than 550 figures, schemes and tables illustrating mechanisms of diverse uneven reactions and stereomutations of chiral compounds - Technical drawings illustrating the conceptual linkage among macroscopic units reminiscent of turnstiles, ratchets, brakes, bevel gears or knots and molecular analogs - greater than 3000 references to motivate extra studying and facilitate extra literature study - A finished thesaurus with stereochemical definitions and phrases which facilitate figuring out and make stronger studying This e-book could be of specific curiosity to undergraduates, graduates and execs operating and discovering within the fields of natural artificial chemistry and analytical chemistry.
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Additional resources for Dynamic stereochemistry of chiral compounds : principles and applications
Example text
Reetz and Stanchev obtained the axial carbinol via organiron(II)-mediated diastereofacial addition of butylmagnesium chloride in 76% de. 33 By contrast, very small nucleophiles such as hydrides or acetylides experience less steric interaction with the remote 4-tertbutyl group and favor the axial approach to avoid local interactions with the axial hydrogens at C-2 and C-6. Reduction of 4-tert-butylcyclohexanone with lithium aluminum hydride proceeds preferentially via axial attack and produces the equatorial alcohol as the major product.
The diastereoselectivity of the Grignard reaction between phenylmagnesium bromide and (S)3-phenylbutan-2-one can be rationalized by looking at the Newman projection of the favored transition state. Since the proton provides less steric hindrance than the methyl substituent, phenylation occurs preferentially from the Si-face, producing (2R,3S)-2,3-diphenylbutan-2-ol in 80% diastereomeric excess. 1. The restricted conformational freedom leads to a highly diastereoselective transition state in which the nucleophile is delivered from the less sterically hindered face exhibiting the smaller ligand S.
As a result, the enantiomers of 2,2 0 -disubstituted biaryls populate two diastereomeric syn- and anti-conformations, with torsion angles in solution usually ranging from 30 to 80 1, and 100 to 150 1, respectively. 6. A well iv Incorporation of sterically demanding substituents into the ortho-positions of biphenyl significantly increases the energy barrier to rotation and favors a near-orthogonal ground state geometry. 1 Ph (S) OMe Me2Mg Me OMe OMgMe H Me Ph OMgMe Si-face attack 99% de Me Mg O OMe (S) OMe Ph (R) CH3 Ph Me favored transition state Cram's chelation rule R′ O H Si-face attack Ph 80% de Ph Mg H Me Ph favored transition state Rationalization of the stereoselectivity of 1,2-nucleophilic additions to chiral ketones, based on Cram’s rule.
Dynamic stereochemistry of chiral compounds : principles and applications by Christian Wolf
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