4.5 Article

Highly Enantioselective Michael Addition of α-Substituted Nitrophosphonates to a Vinyl Sulfone

Journal

SYNTHESIS-STUTTGART
Volume 45, Issue 12, Pages 1654-1658

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/s-0033-1338434

Keywords

thiourea; Michael Addition; cinchona alkaloid; vinyl sulfone; nitrophosphonate

Funding

  1. National University of Singapore [R-143-000-469-112]
  2. Ministry of Education (MOE) of Singapore [R-143-000-494-112]
  3. GSK-EDB [R-143-000-491-592]

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Organocatalytic asymmetric Michael reaction of alpha-substituted nitrophosphonates to phenyl vinyl sulfone catalyzed by cinchona alkaloid-derived tertiary amine-thioureas afforded alpha,alpha-disubstituted nitrophosphonates in very good yields and excellent enantiomeric excesses.

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