4.7 Article

Diastereoselective Synthesis of the Leu-Pro Type Phosphinyl Dipeptide Isostere

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 76, Issue 13, Pages 5472-5476

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo200669r

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Funding

  1. Ministry of Education, Culture, Sports, Science and Technology of Japan
  2. Promotion and Mutual Aid Corporation for Private Schools of Japan
  3. Grants-in-Aid for Scientific Research [21590126] Funding Source: KAKEN

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A diastereoselective synthesis of the Leu-Pro type phosphinyl dipeptide isostere in its protected form was achieved from stereodefined alpha-amino-H-phosphinate. The methodology involved a cross-coupling reaction with alkenyl triflate and subsequent diastereoselective hydrogenation of the alkene moiety, which capitalized on the phosphorus chirality.

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