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Synthesis of a new class of iminosugars based on constrained azaspirocyclic scaffolds by way of catalytic C-H amination.
The synthesis of the first examples of a new class of iminosugars based on constrained spirocyclic scaffolds has been achieved via Rh-catalyzed C(sp(3))-H amination. In this process, the neededExpand
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Catalytic C–H amination at its limits: challenges and solutions
Catalytic C–H amination reactions enable direct functionalization of non-activated C(sp3)–H bonds with high levels of regio-, chemo- and stereoselectivity. As a powerful tool to unlock the potentialExpand
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Synthesis of 4-membered carbasugars by way of stereoselective SmI2-mediated aldehyde-alkene cyclization.
A stereodivergent synthesis of the first examples of 4-membered carbasugars has been achieved from vitamin C by way of an efficient intramolecular SmI2-mediated aldehyde-alkene coupling. In this keyExpand
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Synthesis of spirocyclopropyl γ-lactams by tandem intramolecular azetidine ring-opening/closing cascade reaction: synthetic and mechanistic aspects
Abstract The scope and limitations of a novel intramolecular azetidine ring-opening/closing cascade reaction affording spirocyclopropyl γ-lactams from azetidines in high regio- and stereoselectivityExpand
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The Allyl Cyanate/Isocyanate Rearrangement: An Efficient Tool for the Stereocontrolled Formation of Allylic C–N Bonds
[3,3]-Sigmatropic rearrangements represent powerful methods in the toolbox of synthetic organic chemists for the stereoselective construction of carbon–carbon as well as carbon–heteroatom bonds.Expand
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Total Synthesis of (±)‐Scopolamine: Challenges of the Tropane Ring
Scopolamine was synthesized using 6,7-dehydrotropine as a key intermediate. Rhodium-catalyzed [4 + 3] cycloaddition chemistry and a modified Robinson–Schopf reaction were each independently evaluatedExpand
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Pushing the limits of catalytic C-H amination in polyoxygenated cyclobutanes.
A synthetic route to a new class of conformationally constrained iminosugars based on a 5-azaspiro[3.4]octane skeleton has been developed by way of Rh(ii)-catalyzed C(sp(3))-H amination. The pivotalExpand
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Synthesis of Spirocyclopropyl γ‐Lactams by a Highly Stereoselective Tandem Intramolecular Azetidine Ring‐Opening/Closing Cascade Reaction
A new tandem intramolecular azetidine ring-opening/closing cascade reaction affording spirocyclopropyl γ-lactams in high regio- and stereoselectivity is reported. The key step of the process is an SExpand
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Stereodivergent approach in the protected glycal synthesis of L-vancosamine, L-saccharosamine, L-daunosamine and L-ristosamine involving a ring-closing metathesis step
In this paper, a new access to several chiral 3-aminoglycals as potential precursors for glycosylated natural products is reported from a common starting material, (−)-methyl-L-lactate. TheExpand
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Synthesis of 4‐Membered Carbasugars by Way of Stereoselective SmI2‐Mediated Aldehyde—Alkene Cyclization.
The key step for the synthesis of new carbasugars is reported wherein cyclobutanes with four contiguous asymmetric centers are generated with a high level of stereocontrol.
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