Stereoselective aldol reaction of glutarimides using pseudo C(2) symmetry.
The boron aldol reaction of beta-substituted glutaric imides bearing an oxazolidinone-based auxiliary proceeds with excellent diastereoselectivity; switching the tertiary amine employed between i-Pr(2)EtN or Et(3)N affords enantiomeric lactone product.
Watanabe
Yohsuke
Y
Department of Applied Chemistry, Graduate School of Engineering, Tokyo University of Agriculture and Technology, 2-24-16 Nakacho, Koganei 184-8588, Japan.
Yamazaki
Takashi
T
Kubota
Toshio
T
D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D010881:Piperidones / Q000737:chemistry*; D013237:Stereoisomerism
D007659:Ketones; D010881:Piperidones; C007864:glutarimide