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One‐Pot Tandem Diastereoselective and Enantioselective Synthesis of Functionalized Oxindole‐Fused Spiropyrazolidine Frameworks
Author(s) -
Mei LiangYong,
Tang XiangYing,
Shi Min
Publication year - 2014
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.201403990
Subject(s) - stereocenter , tandem , enantioselective synthesis , oxindole , cycloaddition , combinatorial chemistry , chemistry , catalysis , cascade reaction , organic chemistry , materials science , composite material
A highly efficient palladium(0)‐catalyzed asymmetric [3+2] cycloaddition using 3‐diazooxindoles serving as dipolarophiles affords functionalized pyrazolidine derivatives in an atom‐economical way. In addition, by trapping the pyrazolidine derivatives with maleimides, the corresponding spiropyrazolidine oxindoles containing multiple stereogenic centers have been obtained in high yields along with moderate to good levels of diastereoselectivity and enantioselectivity under mild conditions. Thus, a novel three‐component one‐pot tandem reaction has been developed.