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ASYMMETRIC ENE REACTIONS OF 2-METHYLPROPENE WITH CHLOROALDEHYDES IN THE PRESENCE OF BORONTRIFLUORIDE-L-MENTHYLETHYL ETHERATE
Date
1994-01-01
Author
AKHMEDOV, IM
Tanyeli, Cihangir
AKHMEDOV, MA
MOHAMMADI, M
DEMIR, AS
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The asymmetric ene reactions of prochiral chloroaldehydes, chloral and 2,3-dichlorobutanal with 2-methylpropanal in the presence of BF3 l-menthylethyl etherate gave optically active homoallylic alcohols in 16-22% ee. The dechlorination of the chloro alcohols lead to the unsaturated derivatives of alcohols.
Subject Keywords
Organic Chemistry
URI
https://hdl.handle.net/11511/38796
Journal
SYNTHETIC COMMUNICATIONS
DOI
https://doi.org/10.1080/00397919408013811
Collections
Department of Chemistry, Article
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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
Tanyeli, Cihangir (Elsevier BV, 2005-06-06)
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 ...
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I. AKHMEDOV, C. Tanyeli, M. AKHMEDOV, M. MOHAMMADI, and A. DEMIR, “ASYMMETRIC ENE REACTIONS OF 2-METHYLPROPENE WITH CHLOROALDEHYDES IN THE PRESENCE OF BORONTRIFLUORIDE-L-MENTHYLETHYL ETHERATE,”
SYNTHETIC COMMUNICATIONS
, pp. 137–143, 1994, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/38796.