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Asymmetric synthesis of 1,4-amino alcohol ligands with a norbornene backbone for use in the asymmetric diethylzinc addition to benzaldehyde
Date
2005-06-06
Author
Tanyeli, Cihangir
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The asymmetric synthesis of cis-1,4-amino alcohols with a norbornene backbone was performed starting with (2S,3R)(-)-cis-hemiester 2 (98% ee). Chemoselective amination with NH4OH and HMPTA followed by LAH reduction afforded 5 and 7. respectively. Amido ester 6 was transformed into chiral ligand 9 with Grignard reaction followed by LAH reduction. The chiral ligands 5. 7. and 9 were subjected to asymmetric diethylzinc addition to examine their effectiveness as chiral catalysts. Among these, c chiral ligand 7 exhibited the highest enantioselectivity (88% ee).
Subject Keywords
Physical and Theoretical Chemistry
,
Inorganic Chemistry
,
Organic Chemistry
,
Catalysis
URI
https://hdl.handle.net/11511/41692
Journal
TETRAHEDRON-ASYMMETRY
DOI
https://doi.org/10.1016/j.tetasy.2005.04.019
Collections
Department of Chemistry, Article
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Asymmetric synthesis of novel 1,4-aminoalcohol ligands with norbornene and norbornane backbone: use in the asymmetric diethylzinc addition to benzaldehyde
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The asymmetric synthesis of cis-1,4-aminoalcohols with norbornene and norbornane backbone was performed starting with (2S, 3R)-(-)-cis-hemiester 1 (98% ee). Chemoselective amination with HMPTA followed by Grignard reactions and subsequent LAH reductions afforded compounds 5a-d. cis-Hemiester 1 was also transformed into chiral ligands 7a-f and 9a-d with the DCC coupling method followed by LAH reduction using acyclic, heterocyclic amines and various aniline derivatives and p-toluenesulfonamide, respectively. ...
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C. Tanyeli, “Asymmetric synthesis of 1,4-amino alcohol ligands with a norbornene backbone for use in the asymmetric diethylzinc addition to benzaldehyde,”
TETRAHEDRON-ASYMMETRY
, pp. 2039–2043, 2005, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/41692.