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Volumn 76, Issue 10, 2011, Pages 4194-4199

Highly regio- and diastereoselective anionic [3 + 2] cycloaddition under phase transfer catalytic conditions

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLAMIDES; CATALYTIC CONDITIONS; CYCLOPENTENES; DIASTEREOSELECTIVE; ORGANOCATALYTIC; PHASE TRANSFER; REGIO-SELECTIVE;

EID: 79956124272     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo2005268     Document Type: Article
Times cited : (25)

References (36)
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    • This nomenclature is used to allow the comparison between different methodologies and is not intended to account rigorously for the correct mechanisms
    • This nomenclature is used to allow the comparison between different methodologies and is not intended to account rigorously for the correct mechanisms.
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    • Beak and co-worker did observe conjugated addition with highly activated β-substituted enones, but no cyclization occurred. Moreover, a competitive α- vs γ-addition pathway was observed likely due to equilibrated steps; see ref 9
    • Beak and co-worker did observe conjugated addition with highly activated β-substituted enones, but no cyclization occurred. Moreover, a competitive α- vs γ-addition pathway was observed likely due to equilibrated steps; see ref 9.
  • 23
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    • Except for lithium or magnesium anion derivatives, the generation of allylic sulfone anion under racemic PTC has been sparingly studied. For selected examples
    • Except for lithium or magnesium anion derivatives, the generation of allylic sulfone anion under racemic PTC has been sparingly studied. For selected examples, see: Ogura, K.; Iihama, T.; Kiuchi, S.; Kajiki, T.; Koshikawa, O.; Takahashi, K.; Iida, H. J. Org. Chem. 1986, 51, 700-705
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    • references therein
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    • 2Na in order to generate an allylic sulfone anion; see ref 7.
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    • We previously developed an access to allylic bromide having an acrylamide backbone through two straightforward steps involving an MBH-reaction/ bromination sequence from commercially available acrylamides; see
    • We previously developed an access to allylic bromide having an acrylamide backbone through two straightforward steps involving an MBH-reaction/ bromination sequence from commercially available acrylamides; see: Davoust, M.; Cantagrel, F.; Metzner, P.; Brière, J.-F. Org. Biomol. Chem. 2008, 6, 1981-1993
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    • For recent developments in organocatalysis with sulfones
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    • DBDB was synthesized in one step from dibutylamine and commercially available 2,2′-bis(bromomethyl)-1,1′-biphenyl (see Experimental Section)
    • DBDB was synthesized in one step from dibutylamine and commercially available 2,2′-bis(bromomethyl)-1,1′-biphenyl (see Experimental Section).
  • 35
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    • note
    • Many cinchona derived phase transfer catalysts were tried but did not outperform the Maruokas catalyst. For instance, the best N- anthracenyl cinchonidinium chloride one afforded (NaOH, rt) the cyclopentene 7a in 38% ee and 55% yield. However, this family of catalysts tend to decomposition in our conditions, rendering tedious their development for this methodology.


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