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

…, K Kudo, Y Hashimoto, K Saigo

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

Full Text: HTML

Citation Number: 16

Abstract

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 ...

Related Articles:

… hydroformylation of conjugated dienes catalysed by [(R)-2-diphenylphosphino-1, 1′-dinaphthalen-2′-yl][(S)-1, 1′-dinaphthalene-2, 2′-diyl] phosphite–rhodium (I)

[Horiuchi, Toshihide; Ohta, Tetsuo; Nozaki, Kyoto; Takaya, Hidemasa Chemical Communications, 1996 , # 2 p. 155 - 156]

Alkoxy Radical Cyclizations onto Silyl Enol Ethers Relative to Alkene Cyclization, Hydrogen Atom Transfer, and Fragmentation Reactions

[Rueda-Becerril, Montserrat; Leung, Joe C.T.; Dunbar, Christine R.; Sammis, Glenn M. Journal of Organic Chemistry, 2011 , vol. 76, # 19 p. 7720 - 7729]

Highly stereoselective synthesis of trisubstituted olefins via addition of alkylcopper complexes to acetylenes

[Marfat,A. et al. Journal of Organic Chemistry, 1979 , vol. 44, # 22 p. 3888 - 3901]

More Articles...