Totally stereocontrolled synthesis of α,β-diamino acids by addition of grignard reagents to nitrones derived from L-serine

Tetrahedron Asymmetry

Volumn 9, Issue 4, 1998, Pages 629-646

  Merino, Pedro ^a   Lanaspa, Ana ^a   Merchan, Francisco L ^a   Tejero, Tomas ^a  

^a UNIVERSITY OF ZARAGOZA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

DIAMINO ACID;

ANTIMICROBIAL ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; COLUMN CHROMATOGRAPHY; DERIVATIZATION; DRUG SYNTHESIS; NONHUMAN; PRIORITY JOURNAL; SOLUBILITY; STEREOCHEMISTRY;

EID: 0032570493     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00004-4     Document Type: Article

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42. This tunable selectivity in nucleophilic additions to unsaturated systems has precedents in stereoselective nucleophilic additions to N,N-diprotected and N-monoprotected α-amino aldehydes. See: Dondoni, A.; Perrone, D.; Merino, P. J. Org. Chem. 1995, 60, 8074-8080 and references cited therein.
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46. We have also described the successful application of circular dichroism to the determination of absolute configuration in N-benzylhydroxylamines α-(2-furyl) and α-(2-thiazolyl) substituted; see Tejero, T.; Franco, S.; Junquera, F.; Lanaspa, A.; Merchan, F. L.; Merino, P.; Rojo, I. Tetrahedron: Asymmetry 1996, 7, 1529-1534 and Merchan, F. L.; Merino, P.; Rojo, I.; Tejero, T.; Dondoni, A. Tetrahedron: Asymmetry 1995, 6, 2145-2149, respectively.
47. We have also described the successful application of circular dichroism to the determination of absolute configuration in N-benzylhydroxylamines α-(2-furyl) and α-(2-thiazolyl) substituted; see Tejero, T.; Franco, S.; Junquera, F.; Lanaspa, A.; Merchan, F. L.; Merino, P.; Rojo, I. Tetrahedron: Asymmetry 1996, 7, 1529-1534 and Merchan, F. L.; Merino, P.; Rojo, I.; Tejero, T.; Dondoni, A. Tetrahedron: Asymmetry 1995, 6, 2145-2149, respectively.
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50. (a) Merino, P.; Lanaspa, A.; Merchan, F. L.; Tejero, T. J. Org. Chem. 1996, 61, 9028-9032.
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52. (c) Merino, P.; Merchan, F. L.; Tejero, T. Unpublished crystallographic results; see also Ref. 12. The presence of an intramolecular hydrogen bond has been also confirmed in other α-(tert-butoxycarbonylamino) hydroxylamines; see: Merino, P.; Lanaspa, A.; Merchan, F. L.; Tejero, T. Zeits. Krist. 1997, 212, 323-324 and Merino, P.; Lanaspa, A.; Merchan, F. L.; Tejero, T. Acta Cryst. Sect. C. 1998, 54, 85-86.
53. (c) Merino, P.; Merchan, F. L.; Tejero, T. Unpublished crystallographic results; see also Ref. 12. The presence of an intramolecular hydrogen bond has been also confirmed in other α-(tert-butoxycarbonylamino) hydroxylamines; see: Merino, P.; Lanaspa, A.; Merchan, F. L.; Tejero, T. Zeits. Krist. 1997, 212, 323-324 and Merino, P.; Lanaspa, A.; Merchan, F. L.; Tejero, T. Acta Cryst. Sect. C. 1998, 54, 85-86.
54. (c) Merino, P.; Merchan, F. L.; Tejero, T. Unpublished crystallographic results; see also Ref. 12. The presence of an intramolecular hydrogen bond has been also confirmed in other α-(tert-butoxycarbonylamino) hydroxylamines; see: Merino, P.; Lanaspa, A.; Merchan, F. L.; Tejero, T. Zeits. Krist. 1997, 212, 323-324 and Merino, P.; Lanaspa, A.; Merchan, F. L.; Tejero, T. Acta Cryst. Sect. C. 1998, 54, 85-86.
55. A similar chelation with the carbonyl group of a carbamate moiety has been described for N-(tert-butoxycarbonyl)-α-amino aldehydes. See for example: Garner, P.; Ramakanth, S. J. Org. Chem. 1986, 51, 2609-2612.
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