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2005
Aminocarboxylic acids (hydrazinocarboxylic acids) and esters
P 0270
Asymmetric [2,3]-Rearrangement of Glycine-Derived Allyl Ammonium Ylids. —
glycine salts bearing a camphorsultam auxiliary undergo [2,3] rearrangement
24- 066 N-Allylic
to give allylglycine derivatives with excellent enantiocontrol. Substrates bearing the
(2R)-configured auxiliary afford predominantly (2'S)-configured products, while the
use of the (2S)-auxiliary gives (2'R)-products. Allyl migration is favored over benzyl
migration. For ammonium salts (IX) high diastereoselectivities are observed for the
corresponding products. Ammonium salt (XII) having the chiral auxiliary attached to
the allyl substituent rather than the glycine moiety also undergoes the rearrangement to
give β-ethenyl aspartate derivative (XIII) as major stereoisomer. The route to allylglycine (V) via product (IIb) represents a new and efficient method for this compound.
— (WORKMAN, J. A.; GARRIDO, N. P.; SANCON, J.; ROBERTS, E.; WESSEL, H.
P.; SWEENEY*, J. B.; J. Am. Chem. Soc. 127 (2005) 4, 1066-1067; Dep. Chem.,
Univ. Reading, Whiteknights, Reading, Berkshire RG6 6AD, UK; Eng.) — Klein
2005
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