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Three‐Component Reactions with ( S )‐Methyl Pyroglutamate: An Efficient Way to Diversely Substituted Asymmetric Amidocyclohexenes
Author(s) -
Hübner Sandra,
Michalik Dirk,
Jiao Haijun,
Neumann Helfried,
Klaus Stefan,
Strübing Dirk,
Spannenberg Anke,
Beller Matthias
Publication year - 2007
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.200700031
Subject(s) - stereoselectivity , yield (engineering) , component (thermodynamics) , chemistry , amide , combinatorial chemistry , organic chemistry , computational chemistry , catalysis , materials science , physics , thermodynamics , metallurgy
Chiral N ‐dienyl lactams are crucial building blocks for the synthesis of complex organic compounds. However, their generation is rather challenging. This paper reports the novel one‐pot reaction of ( S )‐methyl pyroglutamate as the a mide component with different a ldehydes and d ienophiles (AAD reaction) to give novel chiral 1‐amido‐2‐cyclohexenes. The corresponding N ‐dienyl lactams generated in situ undergo subsequent Diels–Alder reactions in good yield and diastereoselectivity. The scope and limitations of the three‐component protocol were investigated. X‐ray and NMR spectroscopic analysis of the products as well as DFT calculations of the intermediates were also performed to explain the observed stereoselectivity and structural features.