Enantioselective Hydroxyvinylation with Lithioethenes

Abstract

The enantioselective addition of lithioethenes to aldehydes was studied. Such asymmetric approach of the hydroxyvinylation is reported for the first time with promising ee, (up to 70% at -78 °C in THF), using mixed aggregates of the vinyllithium species and a chiral lithium amide.

mixed aggregates vinyllithiums - chiral lithium amide - asymmetric vinylation

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<A NAME="RG14505ST-13">13</A>

The following may be considered as general procedure for the enantioselective hydroxyvinylation of aldehyde: in a flask A, a 1.7 M solution of t-BuLi in pentane (0.5 mL, 0.85 mmol, 2.1 equiv/1c) was added at -78 °C to a solution of 2-bromovinyltrimethylsilane 1c (90% trans: 78.8 mg, 0.4 mmol, 1 equiv/5) in THF (2 mL) and the resulting mixture was stirred at -78 °C for 1 h then 30 min at -20 °C. In a flask B, a 1.7 M solution of t-BuLi in pentane (0.35 mL, 0.6 mmol, 1 equiv/amine) was added at -78 °C to a solution of (S)-1-benzyl-3-diphenylmethylaminopyrrolidine (205 mg, 0.6 mmol, 1.5 equiv/2c or 5) in THF (1.5 mL) and the resulting mixture was stirred at the same temperature for 1 h. The solution in flask A containing 2c was transferred to flask B and stirred at T °C (see Table [1] ) for 1 h. A solution of aldehyde (0.4 mmol) in THF (1 mL) was added over a period of 20 min (maintaining the temperature at -78 °C) to the mixed aggregate freshly prepared above and the reaction mixture was stirred at -78 °C for 10 h. After addition of brine (10 mL), the organic layer was extracted with Et₂O (3 × 15 mL), dried (MgSO₄), filtered and concentrated. The residue was purified by flash chromatography on silica gel (heptane-EtOAc, 5: 1).

<A NAME="RG14505ST-14">14</A>

Duguet, N.; Paté, F.; Harrison-Marchand, A.; Maddaluno, J.; Oulyadi, H. to be published.

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