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Synthesis of Enantiopure Benzyl Homoallylamines by Indium‐Mediated Barbier‐Type Allylation Combined with Enzymatic Kinetic Resolution: Towards the Chemoenzymatic Synthesis of N‐Containing Heterocycles
Author(s) -
Hietanen Ari,
Saloranta Tiina,
Rosenberg Sara,
Laitinen Evelina,
Leino Reko,
Kanerva Liisa T.
Publication year - 2010
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.200901216
Subject(s) - enantiopure drug , chemistry , kinetic resolution , allylic rearrangement , ring closing metathesis , amide , metathesis , yield (engineering) , stereochemistry , salt metathesis reaction , organic chemistry , combinatorial chemistry , enantioselective synthesis , catalysis , polymerization , polymer , materials science , metallurgy
Barbier‐type indium‐mediated allylations of different N , N ‐(dimethylsulfamoyl)‐protected aldimines with a number of allyl bromides followed by high‐yielding deprotection afforded allylic amines in good to excellent yields. The racemic amines were then subjected to enzymatic kinetic resolution in order to obtain the corresponding ( S )‐amines and ( R )‐amides. When acyl donors with a terminal double bond were applied in the enzymatic kinetic resolution, the product amide could be converted into unsaturated lactams in a straightforward manner by utilizing ring‐closing metathesis. Furthermore, the enantiopure ( S )‐1‐phenylbut‐3‐enylamine was converted into the corresponding diallylamine, which was subjected to ring‐closing metathesis to yield a substituted dehydropiperidine mimicking a number of natural products.