4.8 Article

Concise Synthesis of (+)-allo-Kainic Acid via MgI2-Mediated Tandem Aziridine Ring Opening-Formal [3+2] Cycloaddition

Journal

ORGANIC LETTERS
Volume 15, Issue 16, Pages 4250-4253

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol4020333

Keywords

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Funding

  1. EPSRC
  2. European Research Council (ERC) [246785]
  3. Universita degli studi di Siena
  4. University of Bristol
  5. EPSRC [EP/E052185/1, EP/I038071/1, EP/K03927X/1] Funding Source: UKRI
  6. Engineering and Physical Sciences Research Council [EP/I038071/1, EP/K03927X/1, EP/E052185/1] Funding Source: researchfish

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3-Methyl vinyl aziridine undergoes a mild MgI2-promoted S(N)2' ring opening and concomitant cyclization with fumarate Michael acceptors to give trisubstituted pyrrolidines. The process is efficient and highly diastereoselective. This methodology has been applied to a concise asymmetric synthesis of (+)-allo-kainic acid.

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