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Download e-book for iPad: Topics in Stereochemistry, Volume 13 by Norman L. Allinger, Ernest L. Eliel

By Norman L. Allinger, Ernest L. Eliel

ISBN-10: 0471056804

ISBN-13: 9780471056805

This seminal sequence, first edited by means of Ernest Eliel, accountable for a few of the significant advances in stereochemistry and the winner of the ACS Priestley Medal in 1996, presents assurance of the most important advancements of the sphere of stereochemistry. The scope of this sequence is largely outlined to surround all fields of chemical and organic sciences which are based on molecular and supramolecular interactions. Insofar as chemical, actual, and organic houses are made up our minds by means of molecular form and constitution, the significance of stereochemistry is prime to and consequential for all usual sciences. Topics in Stereochemistry serves as a multidisciplinary sequence that enriches all of chemistry. aimed toward complicated scholars, collage professors and lecturers in addition to researchers in pharmaceutical, agricultural, biotechnological, polymer, fabrics, and wonderful chemical industries, Topics in Stereochemistry publishes definitive and scholarly stories in stereochemistry and has lengthy been well-known because the ultimate reference paintings during this field.

Covering the impact of chirality on all elements of molecular interplay from the elemental actual chemical homes of molecules and their molecular physics to the applying of chirality in new parts comparable to its purposes in fabrics technological know-how, Topics in Stereochemistry explores a large choice of homes, either actual and chemical of isomers to be able to their functions in a few disciplines from biochemistry to fabrics science.

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Additional info for Topics in Stereochemistry, Volume 13

Sample text

R3 M Scheme 4 D. A. EVANS, J. V. NELSON, AND T. R. TABER 19 Table 6 Kinetic Diastereoselection as a Function of the Enolate Ligand RZ (eq. 8 'Condensations carried out at 20°C (EtzO) and times ranging from 5 to 45 min. bDetermined in CC14. (2)-enolate 26 as a function of the steric requirements of the enolate ligand R2 (eq. [ 1 6 ] ) is summarized in Table 6. The continuous change from high levels of erythro diastereoselection for R2 = CH3 (E:T = 1OO:O) t o threo diastereoselection for R2 = t-C4H9 (T:E = 1OO:O) could be ascribed to a crossover from a chair-preferred (tran- sition state C4) to a boat-preferred (transition state B2) process.

A. EVANS, J. V. NELSON, AND T. R. TABER 33 Table 14 Kinetic Aldol Condensations of Enediolate 19 (eq. [27] ). 1 . 2) 1 8-Crown-6 C 45T:45E 70 :30 70 :30 79:21 82: 18 79:21 90: 10 x7:3 acondensations carried out in THF (-50°C, 10 min) in the presence of 2 equiv of chelating agent. bEnolate prepared from the metal naphthalenide. , AS or CS ), with transition state A being preferred on steric grounds. Mulzer has raised the interesting suggestion that highest occupied and lowest unoccupied molecular orbital interactions may be responsible for this preference (17).

It has been argued that transition state gauche interactions between R2 and R, must also be considered (2), but detailed arguments to support this contention, taking into consideration R, * R3 gauche effects for both transition states C, and C2, were not provided. STEREOSELECTIVE ALDOL CONDENSATIONS 18 The basic assumption of the chair-preferred transition state (for tetrahedral metal centers) is clearly tenuous, and diastereomeric boat transition state geometries should not be discounted. For example, the diastereomeric chair and boat transition states for (2)-enolates are illustrated in Scheme 4.

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Topics in Stereochemistry, Volume 13 by Norman L. Allinger, Ernest L. Eliel


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