Synthesis of both enantiomers of phenylglycine using (-)-sparteine

Synlett

Volumn , Issue 7, 1999, Pages 1106-1108

  Barberis, Claude ^a   Voyer, Normand ^a  

^a UNIVERSITÉ LAVAL   (Canada)

Author keywords

( ) Sparteine; Carboxylation; Enantioselective deprotonation; Phenylglycine; Silicon rearrangement

Indexed keywords

BENZYLAMINE; CARBAMIC ACID; DICHLOROMETHANE; ORGANOLITHIUM COMPOUND; PHENYLGLYCINE; SILICON; SOLVENT; SPARTEINE; TRIETHYLAMINE;

ARTICLE; CARBOXYLATION; CHIRALITY; ENANTIOMER; PROTON TRANSPORT; STEREOSPECIFICITY; SYNTHESIS;

EID: 0032797194     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2774     Document Type: Article

References (14)

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2. b) Voyer, N.; Roby, J. Tetrahedron Lett. 1995, 36, 6627.
3. (+)-sparteine is not commercially available. For a leading reference on the use of (-)-sparteine in enantioselective deprotonation see: a) Beak, P.; Basu, A.; Gallagher, D. J.; Park, Y. S.; Thayumanavan, S. Acc. Chem. Res. 1996, 29, 552.;
4. b) Hoppe, D.; Hense, T., Angew. Chem. Int. Ed. Engl. 1997, 36, 2282.
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8. Roby, J.; Voyer, N. Tetrahedron Lett., 1997, 38, 191.
9. 13C NMR and mass spectrometry.
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12. Barberis, C.; Voyer, N. Tetrahedron Lett., 1998, 39, 6807.
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