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Frontispiece: The Brønsted Acid‐Catalyzed, Enantioselective Aza‐Diels–Alder Reaction for the Direct Synthesis of Chiral Piperidones
Author(s) -
Weilbeer Claudia,
Sickert Marcel,
Naumov Sergei,
Schneider Christoph
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Reports
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201780362
Subject(s) - enantioselective synthesis , chemistry , context (archaeology) , phosphoric acid , stereoselectivity , diels–alder reaction , alkylation , catalysis , brønsted–lowry acid–base theory , combinatorial chemistry , organic synthesis , organic chemistry , reactivity (psychology) , domino , substituent , biology , medicine , paleontology , alternative medicine , pathology
The Rapid Assembly of Molecular Complexity… . …ranks among the most important challenges in modern organic chemistry. In their communication on page 513 ff., Schneider et al. have developed a 3‐component, formal aza‐Diels Alder reaction of aldehydes, para ‐anisidine, and a silyl dienolate which assembles a broad range of 2‐piperidones in one synthetic step with excellent enantioselectivity when catalyzed by a chiral phosphoric acid. DFT‐calculations of this process point to a stepwise mechanism comprising a domino‐vinylogous Mannich lactamization reaction. The products were shown to be readily manipulated to furnish poly‐alkylated piperidines. That strategy might prove highly useful in the context of stereoselective alkaloid synthesis.