Asymmetric addition of α-branched cyclic ketones to allenamides catalyzed by a chiral phosphoric acid† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c5sc04202j Click here for additional data file.
نویسندگان
چکیده
We describe the asymmetric addition of unactivated α-branched cyclic ketones to allenamides catalyzed by a chiral phosphoric acid, generating an all-carbon quaternary stereocenter with broad substrate scope and high enantioselectivity. The products are easily transformed into their corresponding 1,5- and 1,4-ketoaldehyde derivatives, which are both important building blocks in organic synthesis.
منابع مشابه
A new approach to the asymmetric Mannich reaction catalyzed by chiral N,N′-dioxide–metal complexes† †Electronic supplementary information (ESI) available. CCDC 1448521 and 1480808.For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c6sc03902b Click here for additional data file. Click here for additional data file.
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A Ni(ClO4)2-catalyzed enantioselective [2 + 2] cycloaddition ofN-allenamides with cyclicN-sulfonylketimines was developed, which regioselectively occurred at the proximal C]C bonds of the N-allenamides. Broad substrate scope of N-allenamides and cyclic N-sulfonylketimines was observed. A range of fused polysubstituted azetidines bearing quaternary stereocenters were afforded in good yields and ...
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Chiral anion phase-transfer of aryldiazonium cations was utilized to achieve highly enantioselective α-amination of carbonyl compounds. A broad scope of indanone- and benzosuberone-derived substrates was amenable to this strategy. Critical to obtaining high levels of enantioselectivity was the use of BINAM-derived phosphoric acids. The utility of this transformation was demonstrated through fac...
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Centro Singular de Investigación en Qúım (CIQUS) and Departamento de Qúımica Compostela, C/ Jenaro de la Fuente s/n, E-mail: [email protected]; fernan Instituto de Qúımica Orgánica General (CS Spain † Electronic supplementary information and experimental procedures. CCDC crystallographic data in CIF or o 10.1039/c5sc00295h ‡ HF and IV equally contributed to this w Cite this: Chem. Sci....
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