Epoxide with methylmagnesium chloride

A further variation in structure can be achieved using diamines such as ethylenediamine or 2,4-toluenediamine. Actually, any starter molecule can be used as a basis for block copolymer, provided the starter molecule contains a labile hydrogen that will react to open a 1,2-epoxide. Usually, such labile hydrogens are defined as being reactive with methylmagnesium chloride to liberate hydrogen in the Zerewitinoff Reaction (160). 

In the same year we achieved the synthesis of the enantiomers of 110, as shown in Figure 4.61.107 (5)-Citronellal was converted to olefinic ester A, which was epoxidized to give B. Treatment of B with isopropylmagnesium chloride in the presence of copper bromide furnished lactone C, which afforded diol D by treatment with methylmagnesium bromide. Finally, Dess-Martin oxidation of D yielded (S)-stigmolone (110), which was in equilibrium with (2R,3S)-1S. Similarly, (7 )-citronellal afforded (7 )-110. ... 

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