(-)-Sparteine-mediated stereoselective directed ortho metalation of ferrocene diamides1

The utility of (-)-sparteine-mediated directed ortho metalation (DoM) has been investigated in stereoselective preparation of planar chiral ferrocenes derived from 1,1'-N,N,N',N'-tetraisopropylferrocenedicarboxamide (5). In the synthesis of C^sub 2^-symmetric analogs of 5, the protoco...

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Bibliographic Details
Published inCanadian journal of chemistry Vol. 84; no. 2; p. 356
Main Authors Laufer, Radoslaw, Veith, Ulrich, Taylor, Nicholas J, Snieckus, Victor
Format Journal Article
LanguageEnglish
Published Ottawa Canadian Science Publishing NRC Research Press 01.02.2006
Subjects
Aldehydes
Chemicals
Chemistry
Engineering research
Industrial research
Palladium
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Summary:The utility of (-)-sparteine-mediated directed ortho metalation (DoM) has been investigated in stereoselective preparation of planar chiral ferrocenes derived from 1,1'-N,N,N',N'-tetraisopropylferrocenedicarboxamide (5). In the synthesis of C^sub 2^-symmetric analogs of 5, the protocol (base, solvent, and two-step DoM) was found to be crucial for obtaining high enantio- and diastereo-selectivities of the products. A variety of highly enantioenriched mono and doubly functionalized derivatives of 5 have been synthesized. The synthetic applications of these compounds as chiral ligands in asymmetric alkylation of aldehydes and asymmetric palladium-catalyzed allylic substitutions have been demonstrated. [PUBLICATION ABSTRACT]
ISSN:0008-4042
1480-3291