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Volumn , Issue 5, 2004, Pages 901-903

Iodine-mediated ring closing alkene iodoamination with N-debenzylation for the asymmetric synthesis of polyhydroxylated pyrrolidines

Author keywords

Conjugate addition; Cyclisation; Debenzylation; Iodoamination; Pyrrolidine

Indexed keywords

ALKENE DERIVATIVE; AMINO ACID DERIVATIVE; BETA AMINO ACID; IODINE; PYRROLIDINE DERIVATIVE;

EID: 1942489284     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-820031     Document Type: Article
Times cited : (44)

References (31)
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    • For instance see: (a) Davies, S. G.; Ichihara, O. Tetrahedron: Asymmetry 1991, 2, 183. (b) Bunnage, M. E.; Chippendale, A. M.; Davies, S. G.; Parkin, R. M.; Smith, A. D.; Withey, J. M. Org. Biomol. Chem. 2003, 3698.
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    • For a related approach to proline derivatives by iodine promoted cyclisations see: (a) Jones, A. D.; Knight, D. W.; Hibbs, D. E. J. Chem. Soc., Perkin Trans, 1. 2001, 1182. (b) Knight, D. W.; Redfern, A. L.; Gilmore, J. J. Chem. Soc., Perkin Trans, 1. 2001, 2874.
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    • For a related approach to proline derivatives by iodine promoted cyclisations see: (a) Jones, A. D.; Knight, D. W.; Hibbs, D. E. J. Chem. Soc., Perkin Trans, 1. 2001, 1182. (b) Knight, D. W.; Redfern, A. L.; Gilmore, J. J. Chem. Soc., Perkin Trans, 1. 2001, 2874.
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    • (a) Readily prepared on a multigram scale from D-ribose; (2R,3R)-2,3-O-isopropylidene pent-4-enal was prepared following the procedure developed by:Paquette, L. A.; Bailey, S. J. Org. Chem. 1995, 60, 7849. (b) Subsequent olefination of the aldehyde under Masamune-Roush conditions gave compound 1: Blanchette, M. A.; Choy, W.; Davis, J. T.; Essenfeld, A. P.; Masamune, S.; Roush, W. R.; Sakai, T. Tetrahedron Lett. 1984, 25, 2183.
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    • 1H NMR spectroscopic analysis of the crude reaction mixture the configuration at C(3) within (3S,4S,5R)-2 was assigned by analogy to the model developed previously to explain the stereoselectivity observed during addition of lithium (R)-N-benzyl-N-α-methylbenzylamide to α,β-unsaturated acceptors, see:Costello, J. F.; Davies, S. G.; Ichihara, O. Tetrahedron: Asymmetry 1994, 5, 3919.
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    • For example see: (a) Fuson, R. C.; Zirkle, C. L. J. Am. Chem. Soc. 1948, 70, 2760. (b) Moragues, J.; Prieto, J.; Spickett, R. G. W.; Vega, A. J. Chem. Soc., Perkin Trans. 1 1976, 938. (c) Cossy, J.; Dumas, C.; Gomez Pardo, D. Eur. J. Org. Chem. 1999, 63, 1693. (d) For recent studies in a related system see: Verhelst, S. H. L.; Martinez, B. P.; Timmer, M. S. M.; Lodder, G.; van der Marel, G. A.; Overkleeft, H. S.; van Boom, J. H. J. Org. Chem. 2003, 68, 9598.
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    • note
    • 1 = 0.045 [I>3σ(I)]. Crystallographic data (excluding structure factors) has been deposited with the Cambridge Crystallographic Data Centre (CCDC 225944).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.