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 Tanyeli, Cihangir; ERDEM, Mine; ÇAKIR, Esen; KESKİN, Eda (Elsevier BV, 2007-09-27) 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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Asymmetric synthesis and molecular docking study of enantiomerically pure pyrrolidine derivatives with potential antithrombin activity Ayan, Seylan; Doğan, Özdemir; Ivantcova, Polina M.; Datsuk, Nikita G.; Shulga, Dmitry A.; Chupakhin, Vladimir I.; Zabolotnev, Dmitry V.; Kudryavtsev, Konstantin V. (Elsevier BV, 2013-07-31) The (2R,4R,5S)- and (2S,4S,5R)-enantiomers of 4-(tert-butyl) 2-methyl 5-(4-bromophenyl)-pyrrolidine-2,4-dicarboxylate 3 were synthesized efficiently with an ee of >90% on a gram scale using a FAM-catalytic methodology. Subsequent modification afforded enantiopure N-((4-chlorophenyl)thio)acetyl pyrrolidine derivatives 4, which are potential thrombin inhibitors according to comprehensive molecular docking studies.

Citation Formats

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.