Dynamic kinetic resolution of (S)-mandelate-derived alpha-bromo esters in nucleophilic substitution and asymmetric syntheses of 3-substituted morpholin-2-ones

作者：Lee Yoon Min; Kang Kyoung Hee; Min Hye Min; Lim Hyun Jin; Park Eun Hyung; Park Yong Sun^*

来源：ARKIVOC, 2010, 1-15.

• Chiral auxiliary
• dynamic kinetic resolution
• nucleophilic substitution
• asymmetric synthesis
• morpholinone

Dynamic kinetic resolution of (S)-mandelate-derived alpha-bromo esters in nucleophilic substitution reaction has been investigated. Substitutions with various alkyl amine nucleophiles in the presence of TBAI and DIEA can provide various alpha-amino esters up to 81% yield and 97:3 dr. Also, the substitution of alpha-bromo esters with N-substituted 2-aminoethanol nucleophiles and following spontaneous cyclization provides a practical protocol for asymmetric syntheses of 3-substituted morpholin-2-ones up to 95:5 er.

• 出版日期2010