Synthesis of rodocaine

Stereocontrolled Synthesis of 3-Sulfonyl Chroman-4-ols

“…On the basis of the results, a plausible mechanism for the formation of 5a is illustrated in Scheme . By in situ coordination of the six-membered ring, palladium chelates with the carbonyl and sulfonyl group of 3a to afford I . Sequentially, a double syn -addition of the enone moiety on I with hydrogen (2 equiv) generates 5a under 2 atm conditions.…”

The Synthesis of Indoline and Benzofuran Scaffolds Using a Suzuki–Miyaura Coupling/Oxidative Cyclization Strategy

“…Our struggles with the generation of 3 from 1 along with the lack of a general synthetic approach to tetrahydro-α-carbolines led us to consider whether a route that started with the piperidine subunit intact might be feasible. This idea ultimately led us to explore the coupling, oxidative cyclization route that is the focus of this letter (Scheme ). − In addition to leading to the synthesis of tetrahydro-α-carbolines, a bonus to our approach is that it has enabled us to extend the targets that are accessible to us to include aminals and benzofurans.…”

Intermolecular [3+2] Cycloaddition of Cyclopropylamines with Olefins by Visible‐Light Photocatalysis

“…The relative configuration of compound 6 d was further confirmed by X-ray crystallography (see the Supporting Information). [22] Given the success of the cycloaddition with styrene, we turned our attention to other olefins to explore the potential of this method (Table 4). Terminal olefins substituted with electron-withdrawing groups underwent the cycloaddition with mono-and bicyclic cyclopropylamines, while internal olefins failed to do so.…”

“…The cyclopentane products obtained from the cycloaddition with monocyclic cyclopropylamines are useful building blocks for preparing fused heterocycles (Scheme 2). [23] For example, the major isomer of 7 d was subjected to the Pdcatalyzed Buchwald-Hartwig amination reaction to furnish fused indoline 8 [24] in 89 % yield. Separately, the major isomer of 7 e was converted into octahydro-1H-cyclopenta[b]pyridine 10 [25] in 71 % overall yield over three steps.…”