Ortho lithiation-in situ borylation of substituted morpholine benzamides

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningfagfællebedømt

Morpholine amides are cheap and safe alternative to Weinreb amides as acylating agents of organometallic species. Herein, the in-situ lithiation/borylation of 18 ortho- meta- and para-substituted morpholine benzamides has been investigated. 10 of the 18 substrates provided the desired boronic esters as the major isomer (>90% regioselectivity) in crude isolated yields ranging from 68 to 93%. The synthetic usability of such building blocks was subsequently illustrated via the synthesis of a kinase inhibitor.

OriginalsprogEngelsk
TidsskriftTetrahedron
Vol/bind73
Udgave nummer12
Sider (fra-til)1576–1582
Antal sider7
ISSN0040-4020
DOI
StatusUdgivet - 23 mar. 2017

ID: 173700828