ASYMMETRIC REDUCTION OF ACETOPHENONE WITH CHIRAL HYDRIDE REAGENT PREPARED FROM LITHIUM ALUMINIUM HYDRIDE AND (S)-2-(ANILINOMETHYL)PYRROLIDINE

1977 ◽  
Vol 6 (7) ◽  
pp. 783-786 ◽  
Author(s):  
Teruaki Mukaiyama ◽  
Masatoshi Asami ◽  
Jun-ichi Hanna ◽  
Susumu Kobayashi
Keyword(s):  
Asymmetric Reduction ◽  
Lithium Aluminium Hydride ◽  
Lithium Aluminium

Asymmetric reduction of p-alkylacetophenones

1986 ◽  
Vol 51 (3) ◽  
pp. 684-686 ◽  
Author(s):  
Otakar Červinka ◽  
Anna Fábryová ◽  
Ivana Brožová ◽  
Miroslav Holík
Keyword(s):  
Asymmetric Reduction ◽  
Optically Active ◽  
Lithium Aluminium Hydride ◽  
Lithium Aluminium

Asymmetric reduction of p-alkylacetophenones Ia-VIIa with lithium aluminium hydride in the presence of (-)-quinine affords optically active alcohols Ib-VIIb of the (R)-(+) configuration in optical yields of about 50%.

Convenient Synthesis of (Z)-7- and (E)-9-dodecene-1-yl Acetate, Components of Some Lepidoptera Insect Sex Pheromone

2017 ◽  
Vol 68 (1) ◽  
pp. 180-185
Author(s):  
Adriana Maria Andreica ◽  
Lucia Gansca ◽  
Irina Ciotlaus ◽  
Ioan Oprean
Keyword(s):  
Sex Pheromone ◽  
Coupling Reaction ◽  
Coupling Scheme ◽  
Lithium Aluminium Hydride ◽  
Terminal Alkyne ◽  
Mercury Derivative ◽  
Lithium Aluminium ◽  
Convenient Synthesis ◽  
Practical Synthesis ◽  
Insect Sex

Were developed new and practical synthesis of (Z)-7-dodecene-1-yl acetate and (E)-9-dodecene-1-yl acetate. The routes involve, as the key step, the use of the mercury derivative of the terminal-alkyne w-functionalised as intermediate. The synthesis of (Z)-7-dodecene-1-yl acetate was based on a C6+C2=C8 and C8+C4=C12 coupling scheme, starting from 1,6-hexane-diol. The first coupling reaction took place between 1-tert-butoxy-6-bromo-hexane and lithium acetylide-ethylendiamine complex obtaining 1-tert-butoxy-oct-7-yne, which is transformed in di[tert-butoxy-oct-7-yne]mercury. The mercury derivative was directly lithiated and then alkylated with 1-bromobutane obtaining 1-tert-butoxy-dodec-7-yne. After acetylation and reduction with lithium aluminium hydride of 7-dodecyne-1-yl acetate gave (Z)-7-dodecene-1-yl acetate with 96 % purity. The synthesis of (E)-9-dodecene-1-yl acetate was based on a C8+C2=C10 and C10+C2=C12 coupling scheme, starting from 1,8-octane-diol. The first coupling reaction took place between 1-tert-butoxy-8-bromo-octane and lithium acetylide-ethylendiamine complex obtaining 1-tert-butoxy-dec-9-yne, which is transformed in di[tert-butoxy-dec-9-yne]mercury. The mercury derivative was directly lithiated and then alkylated with 1-bromoethane obtaining 1-tert-butoxy-dodec-9-yne. After reduction with lithium aluminium hydride of 1-tert-butoxy-(E)-9-dodecene and acetylation was obtained (E)-9-dodecene-1-yl acetate with 97 % purity.

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