4.7 Article

Enantioselective formal alpha-allylation of nitroalkanes through a chiral iminophosphorane-catalyzed Michael reaction-Julia-Kocienski olefination sequence

Journal

CHEMICAL COMMUNICATIONS
Volume 50, Issue 26, Pages 3491-3493

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c3cc49477b

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Funding

  1. NEXT program
  2. JST-CREST
  3. MEXT
  4. Program for Leading Graduate Schools Integrative Graduate Education and Research Program in Green Natural Sciences'' in Nagoya University
  5. Asahi Glass foundation
  6. JSPS

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A two-step sequence for the asymmetric formal alpha-allylation of nitro-alkanes is disclosed. This new methodology relies on the development of a highly diastereo- and enantioselective conjugate addition of nitro-alkanes to vinylic 2-phenyl-1H-tetrazol-5-ylsulfones using chiral triaminoiminophosphorane as a requisite base catalyst and subsequent Julia-Kocienski olefination under kinetic conditions.

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