Catalytic Asymmetric Synthesis and Properties of Fluorinated b2-Amino Acids

2017 Fiscal Year Final Research Report

• Project/Area Number: 16K18856
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Multi-year Fund
• Research Field: Chemical pharmacy
• Research Institution: Microbial Chemistry Research Foundation
• Principal Investigator: NODA Hidetoshi 公益財団法人微生物化学研究会, 微生物化学研究所, 研究員 (40771738)
• Project Period (FY): 2016-04-01 – 2018-03-31
• Keywords: 不斉触媒 / β-アミノ酸 / ペプチド

Outline of Final Research Achievements

This research project aimed at catalytic asymmetric synthesis of beta2-amino acids. Cyclic hydroxylamines were selected as a surrogate for beta-alanine, and used as substrates in the catalytic reactions. Two new catalytic asymmetric transformations have been developed for the synthesis of the building block molecules. One is a Pd-catalyzed decarboxylative allylation, and the other an organocatalytic direct Mannich-type reaction to ketimines. Both transformations produced the corresponding products in highly stereoselective fashion, which were readily converted to beta-amino acid derivatives otherwise difficult to access. Moreover, the products were easily implemented into the standard Fmoc-based solid phase peptide synthesis protocol, providing alpha/beta-hybrid peptides. Beta-Amino acids obtained in this project would find a specific utility in broad chemical areas such as medicinal chemistry and agrochemistry.

Free Research Field

有機化学