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An Easy‐To‐Use, Regioselective, and Robust Bis(amidate) Titanium Hydroamination Precatalyst: Mechanistic and Synthetic Investigations toward the Preparation of Tetrahydroisoquinolines and Benzoquinolizine Alkaloids
Author(s) -
Zhang Zhe,
Leitch David C.,
Lu Man,
Patrick Brian O.,
Schafer Laurel L.
Publication year - 2007
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200600735
Subject(s) - hydroamination , regioselectivity , combinatorial chemistry , titanium , chemistry , organic chemistry , catalysis
Amidate‐supported titanium amido complexes are efficient and regioselective precatalysts for intermolecular hydroamination of terminal alkynes with primary amines. The synthesis and characterization of the first bis(amidate)‐supported titanium‐imido complex is reported. Its role as the active catalytic species is suggested in the course of product distribution studies using deuterated substrates. The bis(amidate)‐supported precatalysts exhibit good functional‐group tolerance, even performing hydroaminations in the presence of ester and amide groups. This functional‐group tolerance was exploited in the synthesis of a variety of 1‐substituted tetrahydroisoquinoline alkaloids and a one‐pot hydroaminative procedure for the high yielding preparation of the benzo[ a ]quinolizine skeleton.