Compound 1 undergoes syn-dihydroxylation to give diastereomers 2 and 3: OH OH OH + HO OH
Chapter 9, Problem 9.89(choose chapter or problem)
Compound 1 undergoes syn-dihydroxylation to give diastereomers 2 and 3: OH OH OH + HO OH HO OH 1 2 3 The ratio of products was found to be highly sensitive to the conditions employed (Tetrahedron Lett. 1997, 38, 50275030). Under typical catalytic conditions (NMO and catalytic OsO4), the ratio of compounds 2 and 3 was found to be 1:4. In contrast, the ratio was observed to be 7:1 under conditions in which stoichiometric amounts of both OsO4 and tetramethylethylene diamine (TMEDA) were used. The investigators noted that TMEDA, a diamine, likely forms a bidentate complex with OsO4 in the manner shown below. Provide an explanation for the observed diastereoselectivity under each set of conditions. d d d+ d+ N N Os O O O O
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