Asymmetric Intramolecular Aza-Michael Reaction in Desymmetrization Processes. Total Synthesis of Hippodamine and epi-Hippodamine

Asymmetric Intramolecular Aza-Michael Reaction in Desymmetrization Processes. Total Synthesis of Hippodamine and epi-Hippodamine

The use of chiral sulfinyl amines both as nucleophilic nitrogen sources and chiral inducers has been described for the first time in a desymmetrization-type process involving an intramolecular aza-Michael reaction. The resulting product was employed as an advanced intermediate in the total synthesis...

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Veröffentlicht in:Organic letters 2015-02, Vol.17 (4), p.960-963
Hauptverfasser: Guerola, Marta, Sánchez-Roselló, María, Mulet, Cristina, del Pozo, Carlos, Fustero, Santos
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container_issue 4
container_start_page 960
container_title Organic letters
container_volume 17
creator Guerola, Marta
Sánchez-Roselló, María
Mulet, Cristina
del Pozo, Carlos
Fustero, Santos
description The use of chiral sulfinyl amines both as nucleophilic nitrogen sources and chiral inducers has been described for the first time in a desymmetrization-type process involving an intramolecular aza-Michael reaction. The resulting product was employed as an advanced intermediate in the total synthesis of the natural product hippodamine and epi-hippodamine, taking advantage of the special symmetry of these molecules. In addition, this is the first asymmetric total synthesis of epi-hippodamine.
doi_str_mv 10.1021/acs.orglett.5b00054
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title Asymmetric Intramolecular Aza-Michael Reaction in Desymmetrization Processes. Total Synthesis of Hippodamine and epi-Hippodamine
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