Oxirane reductive ring opening

Chiral 2-bromoattumols. [iV-(p-Toluenesulfonyl)sulfoximino]oxiranes undergo ring opening to give a-hromoaldehydes which suffer reduction immediately, on exposure to the combination of MgEr and Bu NBH. ... 

A series of l,6-anhydro-2- and -3-deoxy-D-hexopyranoses has been prepared by reductive ring-opening of appropriate oxirans. In a procedure for the synthesis of 3-deoxyaldoses, the monosaccharide benzoylosazone was converted into the 3-deoxyaldosulose by treatment with an aromatic amine base-catalysed... 

Ring opening of oxiranes using azide is followed by Staudinger reduction of the intermediate azido alcohol to give aziridines. 

Phenyl-substituted oxiranes may be reduced in DMF akin to benzyl ethers by direct and indirect methods the regioselectivity is slightly higher in the indirect reduction [76]. Benzoyloxiranes can be reduced in MeCN to aldoles addition of acetic acid prevents a retroaldol reaction catalyzed by the EGB [77]. The ring opening is analogous to the reduction of 2-alkoxyacetophenone to acetophenone. 

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