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Communication | Regular issue | Vol 92, No. 11, 2016, pp.1953-1961
Published online, 29th September, 2016
DOI: 10.3987/COM-16-13562
An Organocatalytic Asymmetric Diels-Alder Strategy for the Enantioselective Synthesis of Spirocyclic Oxindole-Cyclohexenones

Aoi Matsugi, Shiori Nunokawa, Naruhisa Watanabe, Yuya Nakata, Keiji Nakano, Yoshiyasu Ichikawa, and Hiyoshizo Kotsuki*

*Laboratory of Natural Products Chemistry, Faculty of Science, Kochi University, 2-5-1, Akebono-cho, Kochi 780-8520, Japan

Abstract

An efficient method for the asymmetric synthesis of spirocyclic oxindole-cyclohexenone conjugates was developed. A chiral thiourea-catalyzed asymmetric Diels-Alder reaction between 3-alkylidene-oxindoles and Rawal’s diene was used as the key strategy for construction of the desired products in moderate to good yields with good diastereo- and enantioselectivities.