Asymmetric Synthesis of Monofluorinated 1‑Amino-1,2-dihydronaphthalene and 1,3-Amino Alcohol Derivatives

Asymmetric Synthesis of Monofluorinated 1‑Amino-1,2-dihydronaphthalene and 1,3-Amino Alcohol Derivatives

Enantioenriched 1-amino-4-fluoro-1,2-dihydronaphthalene derivatives are accessed via two complementary synthetic strategies. The careful optimization of the reaction conditions required for the elimination step in one route has allowed both the identification of an anchimerically assisted reaction p...

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Veröffentlicht in:Organic letters 2016-03, Vol.18 (5), p.948-951
Hauptverfasser: Lázaro, Rubén, Román, Raquel, Sedgwick, Daniel M, Haufe, Günter, Barrio, Pablo, Fustero, Santos
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container_end_page 951
container_issue 5
container_start_page 948
container_title Organic letters
container_volume 18
creator Lázaro, Rubén
Román, Raquel
Sedgwick, Daniel M
Haufe, Günter
Barrio, Pablo
Fustero, Santos
description Enantioenriched 1-amino-4-fluoro-1,2-dihydronaphthalene derivatives are accessed via two complementary synthetic strategies. The careful optimization of the reaction conditions required for the elimination step in one route has allowed both the identification of an anchimerically assisted reaction pathway and, more importantly, access to a divergent reaction pathway toward fluorinated 1,3-amino alcohols from a common intermediate just by adjusting the number of equivalents of base used.
doi_str_mv 10.1021/acs.orglett.5b03671
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title Asymmetric Synthesis of Monofluorinated 1‑Amino-1,2-dihydronaphthalene and 1,3-Amino Alcohol Derivatives
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