Divergent reactivity of phenol- and anisole-tethered donor-acceptor α-diazoketones

TY - JOUR

T1 - Divergent reactivity of phenol- and anisole-tethered donor-acceptor α-diazoketones

AU - Clarke, Aimee K.

AU - Unsworth, William P.

AU - Taylor, Richard J.K.

N1 - © Elsevier, 2018. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy.

PY - 2018/2/3

Y1 - 2018/2/3

N2 - The first study of the divergent reactivity of phenol/anisole-tethered donor-acceptor α-diazoketones is described. Four distinct product classes were shown to be accessible from closely related α-diazoketone precursors, with the reaction outcome dependent on the nature of the oxygen substituent on the phenol/anisole ring and the catalyst used to decompose the diazo group. Anisole and TBS-protected derivatives selectively produce three products types (cyclopropanes, tetralones and 1,2-dicarbonyls) while phenols selectively produce spirocyclic dienones.

AB - The first study of the divergent reactivity of phenol/anisole-tethered donor-acceptor α-diazoketones is described. Four distinct product classes were shown to be accessible from closely related α-diazoketone precursors, with the reaction outcome dependent on the nature of the oxygen substituent on the phenol/anisole ring and the catalyst used to decompose the diazo group. Anisole and TBS-protected derivatives selectively produce three products types (cyclopropanes, tetralones and 1,2-dicarbonyls) while phenols selectively produce spirocyclic dienones.

KW - Anisole

KW - Buchner reaction

KW - Divergent reactivity

KW - Phenol

KW - α-Diazocarbonyl compounds

UR - http://www.scopus.com/inward/record.url?scp=85044386619&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2018.02.003

DO - 10.1016/j.tet.2018.02.003

M3 - Article

AN - SCOPUS:85044386619

SN - 0040-4020

JO - Tetrahedron

JF - Tetrahedron

ER -