Asymmetric Synthesis and Application of α-Amino Acids by Vadim A. Soloshonok and Kunisuke Izawa (Eds.)

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

content material: New options of designing micro- and nano encapsulation structures --
Micro- and nanoencapsulation for foodstuff applications.

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10), an increase in the amount of water in D M S O decreased both yield and enantioselectivity of the cyclization (entries 11 and 12). Powdered K O H in THF was much less effective than that in D M S O (entries 12 and 13). Powdered K O H in EtOH did not promote cyclization, but rather promoted hydrolysis to give carboxylic acid 49 as a major product in 55% yield (entry 14). The difference in reactivity between powdered K O H in D M S O and powdered K O H in EtOH could be ascribed to the difference in the pKa's of H 0 in these solvents.

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To test the feasibility of F, a cross-over experiment between 9d and 13 was done. 1 equiv of the total amount of 9d and 13) followed by methyl iodide according to the protocol in Table III, affording racemic lOd (79% yield) and (5)-14 (74% ee, 79% yield). This clearly indicates that F is not responsible for the asymmetric induction. OEt O'Bu F The structure and chiral properties of the enolate intermediate were then investigated. 1 equiv) in toluene-THF (4:1) at -78 °C for 30 min followed by /-butyldimethylsilyl (TBS) triflate gave Z-enol silyl ether 23 and its £-isomer 24 in 56% and 27% yield, respectively (Scheme 3).

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