181586-74-3Relevant articles and documents
The total synthesis of (+)-aspicilin using 2,3-butane diacetal protected butane tetrols via a chiral memory protocol
Dixon, Darren J.,Foster, Alison C.,Ley, Steven V.
, p. 1668 - 1680 (2001)
The total syntheses of the polyhydroxylated macrolactone (+)-aspicilin and a diastereoisomer have been achieved via a concise route, starting from the spatially desymmetrized (R′,R′,R,S)-2,3-butanediacetal-protected butane tetrol 13. The key steps include a regioselective silyl protection of 13 and a stereoselective Lewis acid mediated addition of allyltributylstannane to the equatorially disposed aldehyde of 4. Macrocyclization is achieved using ring closing metathesis, after which selective hydrogenation and protecting group removal yields the natural product.
The continuous flow synthesis of butane-2,3-diacetal protected building blocks using microreactors
Carter, Catherine F.,Baxendale, Ian R.,Pavey, John B. J.,Ley, Steven V.
, p. 1588 - 1595 (2010)
The continuous flow synthesis of butane-2,3-diacetal protected derivatives has been achieved using commercially available flow chemistry microreactors in concert with solid supported reagents and scavengers to provide in-line purification systems. The BDA protected products are all obtained in superior yield to the corresponding batch processes.
Synthesis of acetal protected building blocks using flow chemistry with flow I.R. analysis: Preparation of butane-2,3-diacetal tartrates
Carter, Catherine F.,Baxendale, Ian R.,O'Brien, Matthew,Pavey, John B. J.,Ley, Steven V.
, p. 4594 - 4597 (2009)
The syntheses of butane-2,3-diacetal protected tartrate derivatives are described using continuous flow processing techniques with in-line purification and I.R. analytical protocols.
Synthesis of C2-symmetric bisphosphine ligands from tartaric acid, and their performance in the Pd-Catalyzed asymmetric o-allylation of a phenol
Dindaroglu, Mehmet,Akyol Dincer, Sema,Schmalz, Hans-Guenther
supporting information, p. 4315 - 4326 (2014/07/21)
Starting from tartaric acid derived chiral diols or dicarboxylic acid dichlorides with either a 2,2-dimethyl-1,3-dioxolane (Taddol) or a 2,3-dimethoxy-2,3-dimethyl-1,4-dioxane (Tatrol) core structure, and BH 3-protected ortho-phosphanyl phenols, a set of fourteen new C 2-symmetric diphosphine ligands was synthesized. In addition, three related ligands were obtained from ortho-diphenylphosphino-anilines. The fully characterized ligands were then tested in the Pd-catalyzed enantioselective O-allylation of 4-methoxyphenol using crotyl methyl carbonate as a reagent. In addition, a pseudo-intramolecular variant of the reaction, using crotyl 4-methoxyphenyl carbonate as a substrate, was studied. The so-called Trost ligand was used as a reference. Although the Trost ligand (3 mol-%) gave up to 84% ee, one of the new ligands showed higher activity (50% ee with 0.075 mol-%). Copyright
Modification of chiral dimethyl tartrate through transesterification: Immobilization on POSS and enantioselectivity reversal in sharpless asymmetric epoxidation
Garcia, Rafael A.,Van Grieken, Rafael,Iglesias, Jose,Sherrington, David C.,Gibson, Colin L.
experimental part, p. 675 - 683 (2010/09/14)
Modification of dimethyl tartrate has been investigated through transesterification with aminoalcohols to provide reactive functionalities for the covalent bonding of chiral tartrate to polyhedral oligomeric silsesquioxanes. The transesterification of dimethyl tartrate has been widely studied using different catalytic systems and reaction conditions. Through the proper selection of both the catalytic system and the reaction conditions, it is possible to achieve monosubstituted or bis-substituted tartrate derivatives as sole products. All the intermediate chiral tartrate-derived ligands were successfully used in the homogeneous enantioselective epoxidation of allylic alcohols providing moderate enantiomeric excess over the products. Attached amine groups have been used to support the modified tartrate ligands on to a haloaryl-functionalized silsesquioxane moiety. This final chiral tartrate ligand displays reverse enantioselectivity in the asymmetric epoxidation of allylic alcohols with regard to the starting dimethyl tartrate ligand, both molecules having the same chiral sign. However, the POSS-containing ligand can be easily recovered in almost quantitative yield and reused in asymmetric epoxidation reactions. In addition, recovered silsesquioxane-pendant ligand, though displaying decreasing catalytic activity in recycling epoxidation tests, showed very stable enantioselective behavior.
