140459-80-9Relevant academic research and scientific papers
STEREOSPECIFIC C-C-BOND FORMATION WITH RABBIT MUSCLE ALDOLASE - A CHEMOENZYMATIC SYNTHESIS OF (+)-EXO-BREVICOMIN
Schultz, M.,Waldmann, H.,Vogt, W.,Kunz, H.
, p. 867 - 868 (2007/10/02)
(+)-(1S,5R,7S)-Exo-brevicomin 9, a sex pheromone of the western pine bark beetle, is synthesized using an aldol reaction catalyzed by fructose-1,6-diphosphate aldolase (EC 4.1.2.13) from rabbit muscle as the key step by which the absolute configuration of the target is established.
Stereoselective Synthesis of Alcohols, XX. - Diastereoselective Addition of γ-Alkoxyallylboronates to Aldehydes
Hoffmann, Reinhard W.,Kemper, Bruno,Metternich, Rainer,Lehmeier, Thomas
, p. 2246 - 2260 (2007/10/02)
Both the (Z)- and (E)-γ-alkoxysubstituted allylboronates 1 and 3 have been prepared.They add to aldehydes with a diastereoselectivity generally exceeding 90percent to give the syn-(2) and anti-diol derivatives 4, respectively.The structure of one of these adducts has been established by conversion into exo-brevicomin (26).
LIMITED DIASTEREOSELECTIVITY ON ADDITION OF γ-ALKOXY-Z-ALLYLBORONATES TO ALDEHYDES
Hoffmann, Reinhard W.,Kemper, Bruno
, p. 845 - 848 (2007/10/02)
Addition of Z-γ-alkoxy-allylboronates 2 to aldehydes leads to the homoallylalcohls 3 and 4.Increased steric bulk both on the aldehyde part or the allylboronates causes a decrease in diastereoselectivity.The stereochemistry of the addition is established by novel synthesis of exo-brevicomine.
HETEROSUBSTITUTED ALLYLIC CARBANION BASED STEREOCONTROL. REGIO-AND STEREOSELECTIVE REACTION OF O AND S SUBSTITUTED ALLYLIC CARBANIONS WITH ALDEHYDES
Yamamoto, Yoshinori,Saito, Yoshikazu,Maruyama, Kazuhiro
, p. 4959 - 4962 (2007/10/02)
Regio- and diastereoselective reaction of oxygen and sulfur substituted allylic carbanions with aldehydes is described.Either threo or erythro isomer can be obtained predominantly or exclusively by merely choosing an additive.
