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Synlett 2012(1): 137-141  
DOI: 10.1055/s-0031-1290096
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Transesterification of α-Amino Esters Catalyzed by a Tetranuclear Zinc Cluster: Zn4(OCOCF3)6O

Yusuke Maegawaa, Kazushi Agurab, Yukiko Hayashia, Takashi Ohshima*b, Kazushi Mashima*a
a Department of Chemistry, Graduate School of Engineering Science, Osaka University and CREST, JST, Toyonaka,Osaka 560-8631, Japan
e-Mail: mashima@chem.es.osaka-u.ac.jp;
b Graduate School of Pharmaceutical Sciences, Kyushu University and CREST, JST, Higashi-ku, Fukuoka 812-8582, Japan
e-Mail: ohshima@phar.kyushu-u.ac.jp;
Further Information

Publication History

Received 17 August 2011
Publication Date:
09 December 2011 (online)

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Abstract

Transesterification of amino acid ester derivatives was developed using a tetranuclear zinc cluster, Zn4(OCOCF3)6O, as the catalyst. Because the reaction conditions were very mild, a variety of N-protective groups and functional groups on side chains were tolerated.

Key words

transesterification - esters - zinc - amino acids - clusters

    References and Notes

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16

Even in the presence of DMAP base (20 mol%), no epimerization of the products 5ab (>99% ee) and 6ab (98% de) were observed. Only in the case of phenylglycine derivative 10aa, partial epimerization was detected with DMAP additive (99% ee to 63% ee), although the reaction of 10aa did not require the addition of DMAP.

18

No peak corresponding to amide was found in the ¹H NMR spectrum of the crude product before Cbz protection.