Boc-phenylglycine: The reagent of choice for the assignment of the absolute configuration of α-chiral primary amines by 1H NMR spectroscopy

Journal of Organic Chemistry

Volumn 64, Issue 13, 1999, Pages 4669-4675

  Seco, José Manuel ^a   Quiñoá, Emilio ^a   Riguera, Ricardo ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; PHENYLGLYCINE; REAGENT;

ARTICLE; CALCULATION; CHIRALITY; CONFORMATION; ENERGY; MODEL; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0344086176     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo982305q     Document Type: Article

References (18)

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2. Seco, J. M.; Latypov, Sh. K.; Quinoa, E.; Riguera, R. Tetrahedron 1997, 53, 8541-8567.
3. (a) Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512-519.
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14. (b) Trost, B. M.; Bunt, R. C.; Pulley, Sh. R. J. Org. Chem. 1994, 59, 4202-4205.
15. For NMR data of MTPA and MPA amides, see ref 7a and references therein.
16. Haigh, C. W.; Mallion, R. B. Progress in NMR Spectroscopy; Pergamon Press: Ltd.: New York, 1980; Vol. 13, pp 303-344.
17. 3 anti-periplanar to C=O bond, phenyl ring coplanar to Ca-OMe bond). See ref 7a.
18. Main conformers of MPA amides: ap (MeO anti-periplanar to C=O bond, lowest in energy) and sp (MeO syn-periplanar to C=O). See ref 5.