Synlett

Asymmetric synthesis of arylalanines via asymmetric aza-darzens (ADZ) reaction

NE Maguire, AB McLaren, JB Sweeney

Index: Maguire, Naomi E.; McLaren, Andrew B.; Sweeney Synlett, 2003 , # 12 p. 1898 - 1900

Full Text: HTML

Citation Number: 5

Abstract

Abstract (R)-3-Arylalanines may be prepared in high enantiomeric purity from N-dpp imines by a four-step reaction sequence involving asymmetric aza-Darzens reaction, dephosphinylation, hydrogenolysis and hydrolysis. The amino acids thus obtained were of> 95% enantiomeric purity.

Related Articles:

The asymmetric synthesis of. alpha.-amino acids. Electrophilic azidation of chiral imide enolates, a practical approach to the synthesis of (R)-and (S)-. alpha.-azido …

[Evans, David A.; Britton, Thomas C.; Ellman, Jonathan A.; Dorow, Roberta L. Journal of the American Chemical Society, 1990 , vol. 112, # 10 p. 4011 - 4030]

Asymmetric synthesis of monosubstituted and. alpha.,. alpha.-disubstituted. alpha.-amino acids via diastereoselective glycine enolate alkylations

[Williams; Im Journal of the American Chemical Society, 1991 , vol. 113, # 24 p. 9276 - 9286]

Titanium chloride-mediated reactions of the silyl ketene acetals derived from N-methylephedrine esters: an asymmetric variant of the Mukaiyama reaction

[Gennari, Cesare; Colombo, Lino; Bertolini, Giorgio Journal of the American Chemical Society, 1986 , vol. 108, # 20 p. 6394 - 6395]

Palladium-catalyzed reactions in aqueous media. An efficient removal of allyloxycarbonyl protecting group from oxygen and nitrogen

[Genet, Jean Pierre; Blart, Errol; Savignac, Monique; Lemeune, Stephane; Paris, Jean-Marc Tetrahedron Letters, 1993 , vol. 34, # 26 p. 4189 - 4192]

Simple conversion of fully protected amino acids to zwitterions

[Tetrahedron Letters, , vol. 53, # 12 p. 1433 - 1434]

More Articles...