A Diastereodivergent Synthetic Strategy for the Syntheses of Communesin F and Perophoramidine
Organic Letters2014Vol. 16(12), pp. 3316–3319
Citations Over TimeTop 10% of 2014 papers
Seo‐Jung Han, Florian Vogt, Shyam Krishnan, Jeremy A. May, Michele Gatti, Scott C. Virgil, Brian M. Stoltz
Abstract
An efficient, unified, and stereodivergent approach toward communesin F and perophoramidine was examined. The C(3) all-carbon quaternary center of an oxindole was smoothly constructed by base-promoted indolone-malonate alkylation chemistry. The complementary relative stereochemistry of the crucial vicinal quaternary centers found in communesin F and perophoramidine was selectively installed by substrate-controlled decarboxylative allylic alkylations.
Related Papers
- → Lewis Base and Brønsted Base Dual-Catalyzed Formal [4+3] Cycloaddition Reaction: Synthesis of Aza-Spirocycloheptane Oxindole(2016)42 cited
- → ‘On water synthesis’ of oxindoles bearing quaternary carbon center through C–H (sp3) functionalization of methyl azaarenes(2015)33 cited
- → Asymmetric allylic alkylation catalyzed by Pd(II)-complexes with (S)-BINPO, a hemilabile axially chiral P,O-heterodonor inducer(2004)26 cited
- → Highly diastereoselective Claisen rearrangement leading to vicinal quaternary carbons construction of oxindoles(2011)9 cited
- → Novel planar chiral phosphite: Preparation and use in the synthesis of Pd(II) complexes and in Pd-catalyzed allylic alkylation(2007)6 cited