A short synthesis of both enantiomers of trans 3-hydroxypipecolic acid was based on the Suzuki-Miyaura reaction of a lactam-derived enol phosphate and the lipase catalyzed kinetic resolution of the alcohol obtained by hydroboration/oxidation of the coupling product. The RuCl3-catalyzed oxidation of the heteroaryl group introduced by the Suzuki-Miyaura coupling eventually afforded, in six or seven steps, the target compounds in 15-17% overall yield.
A Short, Chemo-Enzymatic Synthesis of Both Enantiomers of trans-3-Hydroxypipecolic Acid / Stefano Begliomini; Lorenzo Sernissi; Dina Scarpi;Ernesto G. Occhiato. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - STAMPA. - 2014:(2014), pp. 5448-5455. [10.1002/ejoc.201402258]
A Short, Chemo-Enzymatic Synthesis of Both Enantiomers of trans-3-Hydroxypipecolic Acid
SERNISSI, LORENZO;SCARPI, DINA;OCCHIATO, ERNESTO GIOVANNI
2014
Abstract
A short synthesis of both enantiomers of trans 3-hydroxypipecolic acid was based on the Suzuki-Miyaura reaction of a lactam-derived enol phosphate and the lipase catalyzed kinetic resolution of the alcohol obtained by hydroboration/oxidation of the coupling product. The RuCl3-catalyzed oxidation of the heteroaryl group introduced by the Suzuki-Miyaura coupling eventually afforded, in six or seven steps, the target compounds in 15-17% overall yield.
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