Asymmetric Synthesis of Congested Spiro-cyclopentaneoxindoles via an Organocatalytic Cascade Reaction

作者:Noole Artur; Ilmarinen Kaja; Jaerving Ivar; Lopp Margus; Kanger Tonis*
来源:Journal of Organic Chemistry, 2013, 78(16): 8117-8122.
DOI:10.1021/jo4008223

摘要

Starting from simple alkylidene oxindoles and nitroketones, a highly stereoselective methodology was developed for the synthesis of spiro-cyclopentaneoxindoles with four consecutive stereogenic centers. Using an organocatalytic cascade of Michael and aldol reactions in the presence of a chiral thiourea catalyst products were obtained in moderate to high yields and excellent enantioselectivities. Nitro, ester, and hydroxyl groups were introduced to the spiro ring, which could be used to facilitate further functionalization of the products.

  • 出版日期2013-8-16