Highly Stereoselective Cationic Cyclization Assisted by a Sulfenyl Group. Scope, Limitation, and Mechanism

…, K Kudo, Y Hashimoto, K Saigo

文献索引：Liu, Changqing; Kudo, Kazuaki; Hashimoto, Yukihiko; Saigo, Kazuhiko Journal of Organic Chemistry, 1996 , vol. 61, # 2 p. 494 - 502

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被引用次数: 16

摘要

When 8-acetoxy-2-methyl-9-(phenylthio)-2-nonene (1a) was treated with an acid, followed by a base, alkylative cyclization proceeded to give a mixture of 1, 2-disubstituted cyclohexanes: 2a, 3a, and 4a. The stereochemistry of the reaction was only slightly affected by the leaving group and the reaction conditions, such as the temperature, solvent, and acid. However, the bulkiness of the sulfenyl group had a great effect on the stereochemical ...