title: Three-component reactions with (S)-methyl pyroglutamate: an efficient way to diversely substituted asymmetric amidocyclohexenes.
abstract: 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 amide component with different aldehydes and dienophiles (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.
authors.affiliation: Leibniz-Institut für Katalyse e.V. an der Universität Rostock, 18059 Rostock, Germany.
authors.forename: Sandra
authors.initials: S
authors.lastname: Hübner
authors.forename: Dirk
authors.initials: D
authors.lastname: Michalik
authors.forename: Haijun
authors.initials: H
authors.lastname: Jiao
authors.forename: Helfried
authors.initials: H
authors.lastname: Neumann
authors.forename: Stefan
authors.initials: S
authors.lastname: Klaus
authors.forename: Dirk
authors.initials: D
authors.lastname: Strübing
authors.forename: Anke
authors.initials: A
authors.lastname: Spannenberg
authors.forename: Matthias
authors.initials: M
authors.lastname: Beller