Novel results from the sodium borohydride reduction of E-3-benzylidene-chromanone epoxides in methanol : formation of an interesting class of chromanone-derived methoxydiols

作者：Mandal Tapas K; Sepay Nayim; Chatterjee Nachiketa; Mallik Asok K^*

来源：Journal of the Indian Chemical Society, 2013, 90(10): 1805-1813.

• E-3-Benzylidenechromanone epoxides
• sodium borohydride reduction
• cis-E-3-benzylidene-4-hydroxychroman epoxides
• 3(S*),4(S*)-dihydroxy-3-[alpha(R*-methoxybenzyl]chromans
• mechanism

Sodium borohydride reduction of a number of E-3-benzylidenechromanone epoxides in methanol gave an interesting class of methoxydidls characterized as 3(S*),4(S*)-dihydroxy-3-[alpha(R*)-methoxybenzyl]chromans, along with the corresponding cis-epoxyalcohols. Mechanistic pathway for the formation of the new type of methoxydiols has been suggested to be methoxide-induced opening of the epoxide ring of an intermediate related to the trans-epoxyalcohols. Sodium borohydride reduction of E-2-benzylidene-1-tetralone epoxide also gave similar results.

• 出版日期2013-10