Science of Synthesis

Ramón, D. J.; Yus, M., Science of Synthesis: Stereoselective Synthesis, (2011) 2, 373.

The diastereoselective addition of chiral organometallics to ketones has been essentially forgotten by researchers because the results were historically very modest.[‌162‌,‌163‌] However, very recently the chiral α,α-difunctionalized organolithium intermediate obtained by deprotonation of oxazolidine (S)-‌39‌ has been added diastereoselectively to various ketones to yield the corresponding alcohols ‌40‌ with good results, as depicted in ‌Table 20‌. The results are good using alkyl aryl ketones, but modest in the case of simple non-aromatic ketones.[‌164‌] ReactIR and NMR spectroscopy show no aggregation evidence for the lithium intermediate.[‌165‌]

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(M)-8-[(8M,8M)-8-Meeeeee-8-(eeeeeeeeeeeeee)-8-eeeeeeeeeeee]-8-eeeeeeeee-8,8-eeeeeeeeeeeeeeeeee-8-eee [(M,M,Me)-‌88‌, M8 = Me; M8 = Me]; Meeeeee Meeeeeeee:[‌888‌]

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References