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Stereoselective synthesis of alcohols, XXXV. Addition of E- and Z-crotylboronates to chiral α-substituted aldehydes (1990)

Brinkmann, Heinrich ; Hoffmann, Reinhard W.

Weinheim : Wiley-Blackwell

Berichte der deutschen chemischen Gesellschaft 123 (1990), S. 2395-2401

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ISSN: 0009-2940

Keywords: Allylboration reaction ; Asymmetric induction ; Calculations, force-field ; Transition-state models ; Chemistry ; Inorganic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: The direction (Cram/anti-Cram) and the extent of asymmetric induction on addition of crotylboronates to a range of chiral aldehydes was investigated. A reversal in the sense of the asymmetric induction on changing from the Z- to the E-crotylboronate was found for aldehydes having polar α substituents and for some of the nonpolar chiral aldehydes. Forcefield calculations on transition-state models reproduced these results in the majority of the cases investigated despite of unaccounted short comings of the method.

Additional Material: 2 Tab.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/cber.19901231223

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