Pyrrolidines from β-Aminoselenides via Radical Cyclization. Diastereoselectivity Control by the N-Substituent

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Abstract

N-Allyl-β-aminoalkyl phenyl selenidesprecursors of 3-aza-5-hexenyl radicalswere prepared by ring opening of N-allylaziridines with benzeneselenol under acidic conditions or by sodium cyanoborohydride reduction of N-allylimines of α-phenylselenenyl ketones. The effect of various N-protective groups (acyl, sulfonyl, or phosphinoyl) on diastereoselectivity in thermally or photochemically initiated 3-aza-5-hexenyl reductive radical cyclization was studied. Whereas N-unprotected derivatives afforded trans-2,4-disubstituded pyrrolidines with good selectivity, the diphenylphosphinoyl group directed cyclization to occur in a highly cis-selective manner.

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This article has been cited by 4 ACS Journal articles (4 most recent appear below).

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  On the Origin of Cis Selectivity in the Cyclization of N-Protected 2-Substituted 3-Aza-5-hexenyl Radicals:  A Density Functional Study

  David Shanks, Stefan Berlin, Magnus Beşev, Henrik Ottosson, and Lars Engman
  The Journal of Organic Chemistry2004 69 (5), 1487-1491

  • On the Origin of Cis Selectivity in the Cyclization of N-Protected 2-Substituted 3-Aza-5-hexenyl Radicals:  A Density Functional Study

    David Shanks, Stefan Berlin, Magnus Beşev, Henrik Ottosson, and Lars Engman
    The Journal of Organic Chemistry2004 69 (5), 1487-1491

    Cyclization of the N-dimethylphosphinoyl-2-methyl-3-aza-5-hexenyl radical has been studied at the UB3LYP/6-31+G(d)//UB3LYP/6-31G(d) hybrid density functional level. The corresponding radical precursor has been synthesized and found to give cis/trans ...

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• 

  Radical Carbonylation/Reductive Cyclization for the Construction of Tetrahydrofuran-3-ones and Pyrrolidin-3-ones

  Stefan Berlin, Cecilia Ericsson, and Lars Engman
  The Journal of Organic Chemistry2003 68 (22), 8386-8396

  • Radical Carbonylation/Reductive Cyclization for the Construction of Tetrahydrofuran-3-ones and Pyrrolidin-3-ones

    Stefan Berlin, Cecilia Ericsson, and Lars Engman
    The Journal of Organic Chemistry2003 68 (22), 8386-8396

    -Hydroxyalkyl aryl chalcogenides obtained by regioselective ring-opening of epoxides with benzeneselenolate or -tellurolate were found to undergo efficient hetero-Michael addition when treated with ethyl propiolate. Subsequent carbonylation/reductive ...

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• 

  Diastereocontrol by a Hydroxyl Auxiliary in the Synthesis of Pyrrolidines via Radical Cyclization

  Magnus Besev and Lars Engman
  Organic Letters2002 4 (18), 3023-3025

  • Diastereocontrol by a Hydroxyl Auxiliary in the Synthesis of Pyrrolidines via Radical Cyclization

    Magnus Besev and Lars Engman
    Organic Letters2002 4 (18), 3023-3025

    Organoselenium precursors of 3-aza-5-hexenyl radicals carrying a 1-hydroxyalkyl group in the 2-position were prepared by addition of organometallic reagents to N-allyl-2-aziridinecarbonitrile, reduction of the resulting aziridine ketone, and ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Diastereocontrol by Trialkylaluminums in the Synthesis of Tetrahydrofurans via Radical Cyclization

  Cecilia Ericsson and Lars Engman
  Organic Letters2001 3 (22), 3459-3462

  • Diastereocontrol by Trialkylaluminums in the Synthesis of Tetrahydrofurans via Radical Cyclization

    Cecilia Ericsson and Lars Engman
    Organic Letters2001 3 (22), 3459-3462

    The influence of various Lewis acids in the radical cyclization of β-allyloxyalkyl phenyl selenides was investigated. Whereas the unperturbed cyclization afforded trans-2,4-disubstituted tetrahydrofurans as the major products (cis/trans ≈ 1/4.5), ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links

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