- Catalytic asymmetric tamura cycloadditions
-
In the presence of a novel, tert-butyl-substituted squaramide-based catalyst, enolizable anhydrides react with alkylidene oxindoles to generate spirooxindole products of significant synthetic interest with excellent enantio- and diastereocontrol. The methodology is of wide scope and encompasses both homophthalic and glutaconic anhydride derivatives, which lead to structurally diverse products. Glutaconic acid-derived anhydrides undergo a clean post-cyclization decarboxylation process which is not a feature of reactions involving homophthalic acid-derived anhydrides. The unusual influence of reaction temperature on diastereocontrol has been probed, with reactions occurring at 30 °C and -30 °C delivering products epimeric at one stereocenter only, in near optical purity. Squared away: The first strategy for bringing about enantioselective Tamura reactions is reported. In the presence of a squaramide-based catalyst, enolizable anhydrides react with alkylidene oxindoles to generate spirooxindole products with excellent enantio- and diastereocontrol. The methodology is of wide scope and leads to structurally diverse products.
- Manoni, Francesco,Connon, Stephen J.
-
supporting information
p. 2628 - 2632
(2014/03/21)
-
- 1,3,6-trihydro-6-aza-3-oxapentalen-2-one derivatives for the treatment of neoplasia
-
1,3,6-Trihydro-6-Aza-3-Oxapentalen-2-One Derivatives for inhibiting neoplastic conditions.
- -
-
-
- Method of preparing 1-alkyl-3-carboxy-1H pyrrole-2-acetic acids
-
An improved method of preparing 1-alkyl-3-carboxy-1H-pyrrole-2-acetic acids, the latter compounds being useful intermediates in the preparation of certain anti-inflammatory 1H-pyrrole-2-acetic acids.
- -
-
-