22089-60-7Relevant articles and documents
Synthesis of functionalized 3,3,9,9-tetramethyl-4,8-diazaundecane-2,10-dione dioximes (propylene amine oximes, PnAOs)
Ramalingam,Zeng,Nanjappan,Nowotnik
, p. 743 - 752 (1995)
The syntheses of several new derivatives of PnAO and their chloronitroso precursors are described. The PnAOs were prepared by an improvement of the reported general procedure. An unexpected product, an isooxalone, was formed while attempting to prepare 1-
Transition state analysis of model and enzymatic prenylation reactions
Lenevich, Stepan,Xu, Juhua,Hosokawa, Ayako,Cramer, Christopher J.,Distefano, Mark D.
, p. 5796 - 5797 (2007)
To obtain a transition state (TS) structure for an enzyme-catalyzed prenylation reaction, SN1 and SN2 model substitution reactions with dimethylallyl chloride were first studied. 13C Kinetic isotope effects (KIEs) for the model reactions were measured by a natural abundance NMR method and used to validate the computational methods that would be used in the subsequent determination of the enzymatic TS structure. Using a primary 13C KIE and a secondary 2H KIE measured via mass spectrometry, a TS structure for the enzyme-catalyzed reaction was computed; a density functional level of electronic structure theory using the mPW1N functional in combination with the 6-31+G(d) basis set was employed for those calculations. That structure has a C-O bond length of 1.69 A and a C-S bond length of 3.70 A. While the former bond length is similar to that for a nonenzymatic SN2 reaction, the latter is considerably (0.90 A) longer, indicating that the enzyme effects catalysis via an "exploded" TS structure. Copyright
A dehydrogenative diels-alder reaction of prenyl derivatives with 2,3-dichloro-5,6-dicyanobenzoquinone
Feng, Hong-Xia,Wang, Yuan-Yuan,Chen, Jie,Zhou, Ling
supporting information, p. 940 - 944 (2015/03/30)
An efficient dehydrogenative Diels-Alder (DHDA) reaction of prenyl derivatives with 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) has been developed under mild conditions, leading to a series of cyclohexene derivatives with good to excellent yields and excellent diastereoselectivity.
Synthesis of N-heterocycles, beta-amino acids, and allyl amines via aza-payne mediated reaction of ylides and hydroxy aziridines
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Page/Page column 52, (2009/01/23)
An ylide-based aza-Payne rearrangement of 2,3-aziridin-1-ols leads to an efficient process for the preparation of pyrrolidines. The aza-Payne rearrangement under the basic reaction conditions favors the formation of epoxy amines. Subsequent nucleophilic attack of the epoxide by the ylide yields a bis-anion, which upon a 5-exo-tet ring closure yields the desired pyrrolidine, thus completing the relay of the 3-membered the 5-membered nitrogen containing ring system. This process takes place with complete transfer of stereochemical fidelity, and can be applied to sterically hindered aziridinols.