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김용환

Kim, Yong Hwan
Enzyme and Protein Engineering Lab.
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Solid-phase synthesis of enantio-controlled lactic acid oligomers

Author(s)
Kim, Seong-HoSim, Yong-KyunKim, Bum-TaeKim, Yong HwanKim, Yeong-JoonPark, SeongsoonLee, Hyuk
Issued Date
2011-07
DOI
10.1016/j.tetasy.2011.08.021
URI
https://scholarworks.unist.ac.kr/handle/201301/20371
Fulltext
http://www.sciencedirect.com/science/article/pii/S0957416611004885
Citation
TETRAHEDRON-ASYMMETRY, v.22, no.14-15, pp.1499 - 1504
Abstract
A synthetic method for lactic acid oligomers via solid-phase synthesis under mild reaction conditions with up to 99% yield is presented. The fine control of the chirality on each lactic acid unit of the oligomers was easily achieved by the substitution of (R)-THP-protected lactic acid (R)-2 by (S)-2 without alternating the procedure. The overall synthesis of the trimer and tetramer was completed in one and two days, respectively. Intramolecular cyclizations of enantio-controlled lactic acids were also attempted through the Yamaguchi macrolactonization or the Mitsunobu reaction. However, we were unable to isolate single cyclic oligomers but always obtained a mixture of cyclic oligomers. (C) 2011 Elsevier Ltd. All rights reserved
Publisher
PERGAMON-ELSEVIER SCIENCE LTD
ISSN
0957-4166

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