73710-76-6Relevant articles and documents
Iridium-Catalyzed Regioselective Hydroalkynylation of Internal Alkenes Directed by an Oxime
Gao, Peng-Chao,Li, Bi-Jie,Wang, Zi-Xuan
supporting information, p. 9500 - 9504 (2021/12/14)
We report here an iridium-catalyzed hydroalkynylation of allylic alcohols protected by an oxime group. Catalytic alkynylation occurs exclusively at the distal position of the alkene. This method generates γ-alkynyl alcohol oximes directly from internal alkenes and terminal alkynes. The oxime group can be readily removed to afford a free alcohol, thus providing an indirect route for the catalytic hydroalkynylation of allylic alcohols.
Diastereoselective alkylations of oxazolidinone vinylogous glycolates
Jiménez, Jacqueline,Meza-León, Rosa L.,Sartillo-Piscil, Fernando,Meléndez, Francisco J.,Sansinenea, Estibaliz,Ortiz, Aurelio
scheme or table, p. 4775 - 4778 (2012/09/08)
A highly Z-selective isomerization (double bond migration) was observed when oxazolidinone vinylogous glycolate was exposed to a strong base to give N-acyl oxazolidinone, bearing an electron rich olefin. The corresponding enolate was exposed to alkyl halides to provide alkylated compounds on the γ-position with respect to OBn group, with high regioselectivity and moderate diastereoselectivity. However, the nature of the chiral oxazolidinone leads to a significant increase in the reaction diastereoselectivity. A stereospecific formation of cis-olefin was also observed in these alkylated compounds.
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 24, (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.
Synthesis of polysubstituted pyrroles
Poulard, Celine,Cornet, Julien,Legoupy, Stephanie,Dujardin, Gilles,Dhal, Robert,Huet, Francois
experimental part, p. 359 - 361 (2010/04/23)
Cross coupling metathesis reactions from two ethylenic compounds 4 and 5 easily led to Michael acceptors 6ab and 7a-b. Reaction of these compounds, or of enone 5', with p-toluenesulfonylmethyl isocyanide (TosMIC) provided the disubstituted pyrroles 9a-c a
