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Asymmetric Enynylation of N ‐Sulfonyl Aldimines Catalyzed by Zn‐BINOL Complexes
Author(s) -
Yang ZhenYan,
Liu TianLin,
Zheng Yan,
Li Shen,
Ma JunAn
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500400
Subject(s) - aldimine , sulfonyl , chemistry , enantioselective synthesis , catalysis , cycloaddition , adduct , yield (engineering) , medicinal chemistry , organocatalysis , organic chemistry , combinatorial chemistry , stereochemistry , metallurgy , alkyl , materials science
An efficient enynylation of N ‐sulfonyl aldimines is described herein. In the presence of Zn‐BINOL complexes, catalytic enantioselective addition reactions of terminal 3‐en‐1‐ynes to N ‐sulfonyl aldimines proceed smoothly to produce enynylated carbinamines in up to 96 % yield and 95 % ee . The adducts are versatile synthetic intermediates that readily undergo Pauson–Khand cycloaddition reactions to give polycyclic products that are otherwise difficult to access.