Stereoselective synthesis of 8-oxabicyclo[3.2.1]octane-2,3,4,6,7-pentols and total asymmetric synthesis of 2,6-anhydrohepturonic acid derivatives and of beta-C-manno-pyranosides suitable for the construction of (1 -> 3)-C,C-linked trisaccharides
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Title serine deriv. I (TBDMS = tert-butyldimethylsilyl; Bn = benzyl) was synthesized from D-serine in excellent overall yield. The reactions of I with Grignard and organocerium reagents were highly stereoselective (Felkin model) to give gamma -hydroxy-beta ...
Chiral auxiliaries and asymmetric catalysis are the workhorses of enantioselective transformations, but they still remain limited in terms of either efficiency or generality. Herein, we present an alternative strategy for controlling the stereoselectivity ...
For the enantioselective diversification of a single starting material, a different chiral catalyst is usually required for each transformation. Herein, we extend the concept of catalytically formed chiral auxiliary from hydrogenation to the asymmetric cyc ...
This review presents an account of the palladium-catalyzed functionalizations of alkenes and alkynes developed at the Laboratory of Catalysis and Organic Synthesis (LCSO). Starting from the intramolecular oxy- and aminoalkynylation of alkenes, tethered met ...
Transition-metal catalyzed C-H functionalizations became a complementary and efficient bond-forming strategy over the past decade. In this respect, Cp*Rh(III) complexes have emerged as powerful catalysts for a broad spectrum of reactions giving access to s ...
Using readily available chiral auxiliaries such as (+)- and (-)-camphanic acid, (R,R)- and (S,S)-tartaric acid derivatives (e.g. RADO(R)-COCl, SADO(R)-COCl) efficient diastereoselective syntheses of rare sugars and glycomimetics have been developed. They e ...
The reaction of 1-(trimethylsilyloxy)cyclopentene (9) with (+/-)-1,3,5-triisopropyl-2-(1-(RS)-{[(1E)-2-methylpenta-1,3-dienyl]oxy}e thyl)benzene ((+/-)-4a) in SO2/CH2Cl2 containing (CF3SO2)(2)NH, followed by treatment with Bu4NF and MeI gave a 3.0:1 mixtur ...
In summary, the development of the catalytically formed chiral auxiliary concept is described. In this approach, an oxazolidine auxiliary is installed via enantioselective Pd catalysis from readily available starting materials in an enantioselective tether ...
Synthesis of orthogonally protected (2S,4R)- and (2S,4S)-4-hydroxyornithines I is reported featuring an asym. alkylation of N-(diphenylmethylene)glycine tert-Bu ester with (5S)-N-benzyloxycarbonyl-5-iodomethyl oxazolidine. Double stereoselection was examd. ...
Pentamethylcyclopentadienyl (Cp*) based transition-metal-catalyzed C-H functionalization has become an important synthetic tool for the construction of molecular complexity from simple starting materials. Despite their high potential, the corresponding asy ...
