Functional rearrangement of 3-Cl or 3,3-diCl-gamma-lactams bearing a secondary 1-chloroalkyl substituent at C-4

TY - JOUR

T1 - Functional rearrangement of 3-Cl or 3,3-diCl-gamma-lactams bearing a secondary 1-chloroalkyl substituent at C-4

AU - Pattarozzi, Mariella

AU - Roncaglia, Fabrizio

AU - Accorsi, Luca

AU - Parsons, Andrew F.

AU - Ghelfi, Franco

PY - 2010/2/6

Y1 - 2010/2/6

N2 - The study of the reaction with MeONa/MeOH of chlorinated gamma-lactams. prepared from the atom transfer radical cyclization of N-allyl-alpha-perchloroamides, has been extended to the case of substiates carrying an exo halogen atom on a branched carbon Only with secondary exo C-Cl groups, that are not located on a fused ring, does the functional rearrangement follow the typical transformation route, Which With trichloro-lactams can proceed further to give 4-alkylidene derivatives From a practical point of view, the outcome of the reaction with di- or trichloio N-cinnamylamides is synthetically valuable, affording the 5-methoxy-IH-pyrrol-2(5H)-one or 3-benzylidenepyrrlidine-2.5-dione. respectively. in good to excellent yield (C) 2009 Elsevier Ltd All rights reserved

AB - The study of the reaction with MeONa/MeOH of chlorinated gamma-lactams. prepared from the atom transfer radical cyclization of N-allyl-alpha-perchloroamides, has been extended to the case of substiates carrying an exo halogen atom on a branched carbon Only with secondary exo C-Cl groups, that are not located on a fused ring, does the functional rearrangement follow the typical transformation route, Which With trichloro-lactams can proceed further to give 4-alkylidene derivatives From a practical point of view, the outcome of the reaction with di- or trichloio N-cinnamylamides is synthetically valuable, affording the 5-methoxy-IH-pyrrol-2(5H)-one or 3-benzylidenepyrrlidine-2.5-dione. respectively. in good to excellent yield (C) 2009 Elsevier Ltd All rights reserved

KW - Halocompound

KW - Radical reactions

KW - gamma-Lactams

KW - Eluminations

KW - Rearrangements

KW - TRANSFER RADICAL CYCLIZATIONS

KW - ATOM-TRANSFER CYCLIZATION

KW - RUTHENIUM-CATALYZED CYCLIZATION

KW - CHAETOMELLIC ANHYDRIDE-A

KW - BOND-FORMING REACTIONS

KW - FORMAL TOTAL SYNTHESIS

KW - GAMMA-LACTAMS

KW - N-ALLYLTRICHLOROACETAMIDES

KW - STEREOSELECTIVE PREPARATION

KW - ATRC REACTIONS

UR - http://www.scopus.com/inward/record.url?scp=73649092754&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2009.11.111

DO - 10.1016/j.tet.2009.11.111

M3 - Article

VL - 66

SP - 1357

EP - 1364

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 6

ER -