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Volumn 69, Issue 5, 2004, Pages 1542-1547

Fine-Tuned Aminal Cleavage: A Concise Route to Differentially Protected Enantiopure syn-α,β-Diamino Esters

Author keywords

[No Author keywords available]

Indexed keywords

ESTERS; REACTION KINETICS; SUBSTRATES;

EID: 1442299987     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035613j     Document Type: Article
Times cited : (43)

References (58)
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    • (b) Cleavage of N-carboxyanhydrides derived from β-lactams: Palomo, C.; Aizpurua, J. M.; Cabré, F.; Cuevas, C.; Munt, S.; Odriozola, J. M. Tetrahedron Lett. 1994, 35, 2725-2728. See also: Palomo, C.; Aizpurua, J. M.; Gamboa, I.; Carreaux, F.; Cuevas, C.; Maneiro, E.; Ontoria, J. M. J. Org. Chem. 1994, 59, 3123-3130 See also: Palomo, C.; Aizpurua, J. M.; Galarza, R.; Mielgo, A. Chem. Commun. 1996, 633-634.
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    • note
    • (e) From regioselective ring opening of an aziridine obtained via Sharpless asymmetric aminohydroxylation: see ref 2a.
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    • note
    • (f) From (E)-α,β-bis(N-acylamino)acrylates by enantioselective hydrogenation: see ref2b.
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    • (g) From a protected L-serine-derived nitrone by addition of Grignard reagents: see ref 2c.
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    • 3: see ref 2i.
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    • (i) From enamides by enantioselective hydrogenation: see ref 2j.
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    • (k) Direct diamination of olefins: Muñiz, K.; Nieger, M. Synlett 2003, 211-214.
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    • note
    • A detailed account of these experiments is included in the Supporting Information.
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    • note
    • 1 = H, Ar = Ph) to p-toluensulfonimine did not render N-tosylimidazolidines related to 1a and 1b but a mixture of racemic N-sulfonyldiamino esters with poor selectivity (syn:anti = 70:30); see ref 5b.
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    • note
    • We also reconsidered the use of acidic conditions to hydrolyze imine C; however, addition of different acids to the reaction mixture gave erratic mixtures of imidazolidines and diamino esters probably due to uncontrolled cyclization of the latter with benzaldehyde during the workup process.
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    • note
    • For full details of all these experiments, see the Supporting Information.
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    • For an isolated example of α-substituted β-unsubstituted derivatives, see: Hartwig, W.; Mittendorf, J. Synthesis 1991, 939-941.
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    • 2O, rt to reflux or TFA, MeOH, rt to reflux.
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    • For a related procedure for the synthesis of piperidines from p-tolylsulfinimines, see: Davis, F. A.; Prasad, K. R.; Nolt, M. B.; Wu, Y. Org. Lett. 2003, 5, 925-927.
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    • 2 = Bn), see the Supporting Information.
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    • For a recent reference, see: Hulme, A. N.; Montgomery, C. H.; Henderson, D. K. J. Chem. Soc., Perkin Trans. 1 2000, 1837-1841. See also: Reetz, M. T.; Drewes, M. W.; Schwickardi, R. Org. Synth. 1998, 76, 110-122.
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    • A small amount (<10%) of a tribenzylated derivative, 6c′, was obtained upon dibenzylation of 3c. For full details see the Supporting Information.
  • 58
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    • note
    • 1H NMR spectrum.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.