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Efficient Synthesis of Polycyclic γ‐Lactams by Catalytic Carbonylation of Ene‐Imines via Nickelacycle Intermediates
Author(s) -
Hoshimoto Yoichi,
Ashida Keita,
Sasaoka Yukari,
Kumar Ravindra,
Kamikawa Ken,
Verdaguer Xavier,
Riera Antoni,
Ohashi Masato,
Ogoshi Sensuke
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201703187
Subject(s) - carbonylation , chemistry , catalysis , cycloaddition , carbon monoxide , nickel , ene reaction , combinatorial chemistry , carbon atom , organic chemistry , medicinal chemistry , stereochemistry , ring (chemistry)
Abstract The nickel(0)‐catalyzed carbonylative cycloaddition of 1,5‐ and 1,6‐ene‐imines with carbon monoxide (CO) is reported. Key to this reaction is the efficient regeneration of the catalytically active nickel(0) species from nickel carbonyl complexes such as [Ni(CO) 3 L]. A variety of tri‐ and tetracyclic γ‐lactams were thus prepared in excellent yields with 100 % atom efficiency. Preliminary results on asymmetric derivatives promise potential in the synthesis of enantioenriched polycyclic γ‐lactams.