TheN-Benzylirninederivedfrom2,3-di-O-benzyl-D-glyceraidehyde reactswithDanishefsky's diene to afford the correspondinghetero Diels-Alder adductwith a high diaatereoaelectivity. This compoundcanbe.transformed to enantiomerically pure(2R)40xopipecolicacid 01997 EIsevierScienceLtd. The piperidine ring
✦ LIBER ✦
Reversal of the stereochemical course of the addition of phenylmagnesium bromide to N-benzylimines derived from R-glyceraldehyde depending on the O-protecting group and its application to the synthesis of both enantiomers of phenylglycine
✍ Scribed by Ramón Badorrey; Carlos Cativiela; María D. Díaz-de-Villegas; JoséA. Gálvez
- Publisher
- Elsevier Science
- Year
- 1997
- Tongue
- French
- Weight
- 380 KB
- Volume
- 53
- Category
- Article
- ISSN
- 0040-4020
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Asymmetric Hetero Diels-Alder Reaction of N-Benzylimines Derived from ( R)-Glyceraldehyde: A New Approach to Homochiral Piperidine Building Blocks and Its Application to the Synthesis of (2R)-4-Oxopipecolic Acid. -The D-glyceraldehyde derived N-benzyl imine (I) undergoes a highly diastereoselective