Laieb, TaouesChastanet, JacquelineZhu, Jieping2010-11-252010-11-252010-11-25199810.1021/jo971468whttps://infoscience.epfl.ch/handle/20.500.14299/58537Title serine deriv. I (TBDMS = tert-butyldimethylsilyl; Bn = benzyl) was synthesized from D-serine in excellent overall yield. The reactions of I with Grignard and organocerium reagents were highly stereoselective (Felkin model) to give gamma -hydroxy-beta -amino alcs. II (R = CHMe2, Me, Ph, Bu) in good yield. Transformation of II (R = CHMe2) into (2S,3S)-beta -hydroxyleucine (III) is also reported. [on SciFinder (R)]Alcohols Role: SPN (Synthetic preparation)PREP (Preparation) (aminohydroxy; diastereoselective synthesis of hydroxy amino alcs. and hydroxyleucine via addn. of Grignards and organocerium reagents to chiral serine aldehyde); Glycols Role: SPN (Synthetic preparation)PREP (Preparation) (amino; diastereoselective synthesis of hydroxy amino alcs. and hydroxyleucine via addn. of Grignards and organocerium reagents to chiral serine aldehyde); Asymmetric synthesis and induction (diastereoselective synthesis of hydroxy amino alcs. and hydroxyleucine via addn. of Grignards and organocerium reagents to chiral serine aldehyde); Addition reaction; Addition reaction (nucleophilicstereoselective; diastereoselective synthesis of hydroxy amino alcs. and hydroxyleucine via addn. of Grignards and organocerium reagents to chiral serine aldehyde)asym synthesis hydroxy amino alc; stereoselective Grignard dibenzylserine aldehyde prepn; organocerium stereoselective addn dibenzylserine aldehyde prepntext::journal::journal article::research article