(-)-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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| Published in | Canadian journal of chemistry Vol. 84; no. 2; p. 356 |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
Ottawa
Canadian Science Publishing NRC Research Press
01.02.2006
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| Subjects | |
| Online Access | Get full text |
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| 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 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] |
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| AbstractList | 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] |
| Author | Laufer, Radoslaw Taylor, Nicholas J Snieckus, Victor Veith, Ulrich |
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| Copyright | Copyright National Research Council of Canada Feb 2006 |
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| Title | (-)-Sparteine-mediated stereoselective directed ortho metalation of ferrocene diamides1 |
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