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- Title
(–)-Sparteine-mediated stereoselective directed ortho metalation of ferrocene diamides.
- Authors
Laufer, Radoslaw; Veith, Ulrich; Taylor, Nicholas J.; Snieckus, Victor
- Abstract
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 C2-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.
- Subjects
ORGANOMETALLIC chemistry; SPARTEINE; FERROCENE; ALKYLATION; ALDEHYDES
- Publication
Canadian Journal of Chemistry, 2006, Vol 84, Issue 2, p356
- ISSN
0008-4042
- Publication type
Article
- DOI
10.1139/V06-008