Asymmetric [2,3]-rearrangement of glycine-derived allyl ammonium ylids.
The first examples of highly enantioselective [2,3]-sigmatropic rearrangements of acyclic allylic ammonium ylids are reported. Thus, a range of N-{2'-[(N'-allyl-N',N'-dialkyl)ammonium]}acetyl camphor sultams undergo rearrangement at 0 degrees C in DME solution with high diastereofacial control (up to 99:1 dr) to give allylglycines in generally high yield. The power of the method has been demonstrated in a rapid and efficient synthesis of (R)-allyl glycine.
Workman
James A
JA
School of Chemistry, University of Reading, Reading RG6 6AD, UK, and Hoffmann-La Roche, Ltd., Discovery Chemistry, 4070-Basel, Switzerland.
Garrido
Neil P
NP
Sançon
Julien
J
Roberts
Edward
E
Wessel
Hans Peter
HP
Sweeney
J B
JB
D000498:Allyl Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D000501:Allylglycine / Q000138:chemical synthesis / Q000737:chemistry; D005998:Glycine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D000644:Quaternary Ammonium Compounds / Q000737:chemistry*
D000498:Allyl Compounds; D000644:Quaternary Ammonium Compounds; D000501:Allylglycine; D005998:Glycine