An asymmetric pericyclic cascade approach to 3-alkyl-3-aryloxindoles: generality, applications and mechanistic investigations

作者：Richmond Edward; Ling Kenneth B; Duguet Nicolas; Manton Lois B; Celebi Olcum Nihan; Lam Yu Hong; Alsancak Sezen; Slawin Alexandra M Z; Houk K N^*; Smith Andrew D

来源：Organic and Biomolecular Chemistry, 2015, 13(6): 1807-1817.

DOI：10.1039/c4ob02526a

The reaction of L-serine derived N-arylnitrones with alkylarylketenes generates asymmetric 3-alkyl-3-aryloxindoles in good to excellent yields (up to 93%) and excellent enantioselectivity (up to 98% ee) via a pericyclic cascade process. The optimization, scope and applications of this transformation are reported, alongside further synthetic and computational investigations. The preparation of the enantiomer of a Roche anti-cancer agent (RO4999200) 1 (96% ee) in three steps demonstrates the potential utility of this methodology.

• 出版日期2015