Applied Mathematicsematics

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By Vadim A. Soloshonok and Kunisuke Izawa (Eds.)

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26. 27. 28. 29. 30. C Chapter 3 Asymmetric Synthesis of Amino Acids with a Tetrasubstituted Carbon Center via Memory of Chirality Takeo Kawabata Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan Asymmetric synthesis of amino acid derivatives with a tetrasubstituted carbon center via memory of chirality is described. Intermolecular and intramolecular alkylation of αamino acid derivatives proceeded highly enantioselectively in the absence of external chiral sources. The key intermediates for the asymmetric induction were chiral enolates with dynamic axial chirality.

2006, 39, 451-463 and references therein. ; Aldhoun, M . J. Org. Chem. 2007, 72, 7677-7687. C 18. 19. 20. 21. 22. 23. 24. 25. 26. 27. 28. 29. 30. C Chapter 3 Asymmetric Synthesis of Amino Acids with a Tetrasubstituted Carbon Center via Memory of Chirality Takeo Kawabata Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan Asymmetric synthesis of amino acid derivatives with a tetrasubstituted carbon center via memory of chirality is described. Intermolecular and intramolecular alkylation of αamino acid derivatives proceeded highly enantioselectively in the absence of external chiral sources.

Numbers in the brackets indicate ee of the product obtained by the reaction with KHMDS in DMF at -60 °C. 2 44 Examples of asymmetric cyclization of various amino acid derivatives via enantioselective intramolecular C-C bond are shown in Table V . Fivemembered cyclization of phenylalanine, tyrosine, methionine, valine, and alanine derivatives took place by treatment with K H M D S in D M F - T H F (4:1) at -60 °C for 30 min to give a-substituted prolines in 94-98% ee (entries 1-5). The four- and six-membered cyclization of phenylalanine derivatives 37 and 39 took place in high enantioselectivity to give azetidine 38 and piperidine derivatives (40) in 95% and 97% ee, respectively (entries 6 and 7).

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