Abstract
The chiral reagents (+)- and (−)-(Ipc)2BOTf are used to control the aldol addition reactions of ethylketone3 with methacrolein. Under suitable conditions, racemic3 can be converted into the SS aldol adduct (+)-4 in ≥95% ee with >95% diastereoselectivity. Resolved starting ketone (+)-3 can be recovered in ≥95% ee. Adduct (+)-4 was converted into the rifamycin S segment (−)-2via stereoselective ketone reduction and hydroboration.
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