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).
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.
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.
