A Simple Recipe for Sophisticated Cocktails: Organocatalytic One‐Pot Reactions—Concept, Nomenclature, and Future Perspectives

Abstract

Asymmetric organocatalysis has been successfully incorporated in many multistep one-pot sequences to provide simple access to structurally complex target molecules in a highly stereoselective fashion. The key feature behind this success is the ability of organocatalyzed reactions to proceed efficiently in the presence of large amounts of spectator reagents. Additionally, owing to their organic nature and substoichiometric presence, organocatalysts are also expected to become innocent bystanders in subsequent transformations. In this Minireview, an easy-to-use classification and nomenclatural system that is capable of systematically and informatively describing each one-pot reaction is introduced, and selected important contributions within the field of organocatalytic one-pot reactions are reviewed according to this new system. Finally, future developments and perspectives in the field are discussed.

Multi-Bond Forming Processes in Efficient Synthesis

“…Tietze and Beifuss have defined 'domino' and 'consecutive' reactions [9] in order to draw a distinction between those processes that involve either a single or multiple synthetic operations. [10] Thus, a domino reaction has been defined as 'a transformation of two or more bond-forming reactions under identical reaction conditions, in which the latter transformations take place at the functionalities obtained in the former bond forming reactions'. [11] Domino reactions are the ultimate expression of synthetic orchestration and execution.…”

One-Pot Two-Step Organocatalytic Asymmetric Synthesis of Spirocyclic Piperidones via Wolff Rearrangement–Amidation–Michael–Hemiaminalization Sequence

“…Over the past decade, asymmetric organic catalysis [2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17], quite powerful for synthesizing various heterocyclic molecules, has formed the basis of several elegant approaches to construct chiral single-heterocycle piperidine skeletons with high efficiency and low toxicity under environmentally friendly conditions . In contrast, relatively few organocatalytic methods have been described to stereo-selectively form spirocyclic piperidine derivatives [30][31][32][33][34][35][36], particularly ones with a quaternary stereocenter [37][38][39].…”

Enantioselective Organocatalysis in Microreactors: Continuous Flow Synthesis of a (S)-Pregabalin Precursor and (S)-Warfarin

“…The extremely fast growth of metal-free catalytic methodologies and novel organocatalytic stereoselective transformations has opened new avenues in the synthesis of complex chiral molecules, and has offered unique possibilities to develop more sustainable processes [17]. Since organocatalysis involves simple organic molecules as catalysts, the contamination of final products with heavy metals is intrinsically avoided; thus, the combination of organocatalysis with flow chemistry would represent an effective methodology for the synthesis in continuo of enantiomerically pure APIs.…”