Die Strukturdynamik von Pentadienylmetall-Verbindungen mit endständiger Alkyl-Gruppe : zugleich "stereoselektive" und "stereodefensive" Synthese eines natürlichen Riechstoffes
Stereospecific metalation of (Z)- and (E)-1,4-decadiene with BuLi or BuLi-Me3COK followed by dimethoxyborylation and oxidn. gave (Z,E)-, (E,Z)-, and (E,E)-isomers of 2,4-decadien-1-ol (I), and the 4th isomer, (Z,Z)-I, was prepd. by hydrogenation of 2,4-decadiyn-1-ol. The isovalerates of all 4 I isomers and of (E,Z)-2,4-undecadien-1-ol were prepd. (E,Z)-I isovalerate is a natural flavor component. [on SciFinder (R)]
1980
63
8
2393
403
CAN 94:208312
23-17
Aliphatic Compounds
Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz.
Journal
written in German.
106-95-6 Role: RCT (Reactant), RACT (Reactant or reagent) (Grignard reaction of, with 1-octyne); 629-05-0 Role: RCT (Reactant), RACT (Reactant or reagent) (Grignard reaction of, with allyl bromide); 108-12-3 Role: RCT (Reactant), RACT (Reactant or reagent) (esterification of, with unsatd. alcs.); 24948-66-1 Role: RCT (Reactant), RACT (Reactant or reagent) (hydrogenation of); 77657-83-1 Role: RCT (Reactant), RACT (Reactant or reagent) (hydroxymethylation of); 109-72-8 Role: RCT (Reactant), RACT (Reactant or reagent) (metalation with, of decadiene, stereospecific); 865-47-4 Role: RCT (Reactant), RACT (Reactant or reagent) (methylation with butyllithium and, of decadiene, stereospecific); 19821-86-4P; 31508-11-9P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and hydrogenation of); 55976-14-2P; 71612-10-7P; 77657-80-8P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. and metalation-dimethoxyborylation-oxidn. of); 66725-78-8P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and reaction of, with hexyltriphenylphosphonium bromide and butyllithium); 77663-37-7P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and redn. of); 16195-71-4P; 18409-21-7P; 56699-32-2P; 57022-74-9P; 77657-76-2P; 77657-77-3P; 77657-78-4P; 77657-79-5P; 77657-81-9P; 77657-82-0P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of); 68-12-2 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with (propynyloxy)tetrahydropyran); 6089-04-9 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with DMF); 4762-26-9 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with butyllithium and (tetrahydropyranyloxy)butynal)
REVIEWED
EPFL