RT Journal Article
T1 Synthesis of Highly Substituted Enantiopure Piperazines and Ketopiperazines from Vicinal N-Sulfinyl Diamines
A1 Flores Aguilar-Amat, Aída
AB Enantiopure 1-benzyl-2,3-disubstituted piperazines (4) have been synthesized by treatment of N-sulfinyl-N-benzyldiamino alcohols (1) with diethyl oxalate and sodium methoxide followed by reduction with borane. Alternatively, the sulfinamido group was preserved by an N-acylation/cyclization protocol using α-chloroacetyl chloride that led to the synthesis of N-sulfinyl ketopiperazines (11). Ensuing elimination of the sulfinyl group with NaH produced imino ketopiperazines (9) that are suitably functionalized for nucleophilic addition to the imino moiety. Stereoselective and high yielding allylation of imino ketopiperazines (9c) was achieved under Barbier conditions using CeCl3·7H2O as the additive.
PB American Chemical Society
SN 0022-3263
YR 2006
FD 2006-01-14
LK https://hdl.handle.net/20.500.14352/98354
UL https://hdl.handle.net/20.500.14352/98354
LA eng
NO Comunidad de Madrid
NO Dirección General de Investigación Científica y Técnica
DS Docta Complutense
RD 8 abr 2025