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Enantioselective Palladium‐Catalyzed N‐Allylation of Lactams
Author(s) -
Visse Robin,
Fidan Mesut,
Götzinger Alissa,
Motzny Angelika,
Jeddi Samir,
Braun Manfred
Publication year - 2018
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201801233
Subject(s) - enantioselective synthesis , palladium , catalysis , deprotonation , chemistry , stereochemistry , medicinal chemistry , combinatorial chemistry , organic chemistry , ion
N‐Deprotonated five‐, six‐, seven, and nine‐membered lactams undergo smooth palladium‐catalyzed N‐allylation with methyl‐(pent‐3‐en‐2‐yl)‐carbonate or 2‐chloro‐3‐pentene. With axially chiral bisphosphane ligands, enantioselectivities ranging from 83 to 97% ee are reached. The configuration of one of the allylation products is assigned unambiguously by the preparation of a relay compound and by analogy to the others. Using the enantioselective allylation protocol as a key step, δ‐valerolactam is converted into (4 S ,9a R )‐4‐methylquinolizidine.