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Note | Regular issue | Vol 51, No. 3, 1999, pp.639-647
Published online, 1st January, 1970
DOI: 10.3987/COM-98-8438
Diastereoselectivity in the Methylation and Reduction of 3-Aryl-3a,4,5,6,7,7a-hexahydro-1,2-benzisoxazol-4-ones

Hyoung Rae Kim,* Hyun Ju Park, Seung Il Shin, Byung Hee Lee, Jae Nyoung Kim, and Eung K. Ryu

*Bioorganic Science Division, Korea Research Institute of Chemical Technology, P.O. Box 107, Yousung, Taejeon, 305-600, Korea

Abstract

Various 3-aryl-3a,4,5,6,7,7a-hexahydro-1,2-benzisoxazol-4-ones were methylated at 3a-positions and reduced by NaBH4 to afford the corresponding 3a,4-cis-3a,7a-cis-3a-methyl-3a,4,5,6,7,7a-hexahydro-1,2-benzisoxazo1-4-ols with excellent diastereoselectivity. The resulting hexahydro-1,2-benzisoxazol-4-ols were easily converted to the corresponding 2-aroyl-2-rnethylcyclohexane-1,3-diols by catalytic hydrogenation with Raney Ni.