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Organische Synthesen mit Übergangsmetallkomplexen, 70. [2‐(Galactopyranosylamino)ethenyl]carben‐ und 3‐(Galactopyranosylamino)‐1,2‐propadienyliden‐Komplexe durch 3‐Addition von 2,3,4,6‐Tetra‐ O ‐pivaloyl‐β‐D‐galactopyranosylamin an Alkinylcarben‐Komplexe (M = Cr, W). — Atropisomere Galactopyranosyl‐Pyrrole durch Reaktion von [2‐(Galactopyranosylamino)ethenyl]carben‐Komplexen mit Isocyaniden
Author(s) -
Aumann Rudolf
Publication year - 1994
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19941270423
Subject(s) - chemistry , carbene , isocyanide , tetra , atropisomer , ketene , stereochemistry , medicinal chemistry , enantiomer , transition metal , catalysis , organic chemistry
Organic Syntheses via Transition Metal Complexes, 70 [1] . — [2‐(Galactopyranosylamino)ethenyl]carbene and 3‐(Galactopyranosylamino)‐1,2‐propadienylidene Complexes on 3‐Addition of 2,3,4,6‐Tetra‐ O ‐pivaloyl‐β‐D‐galactopyranosylamine to Alkynylcarbene Complexes (M = Cr, W). — Atropisomeric Galactopyranosyl Pyrroles by Reaction of [2‐(Galactopyranosyl‐amino)ethenyl]carbene Complexes with Isocyanides Enantiomeric pure (2‐aminoethenyl)carbene complexes L n MC(OEt)CHC(Ph)NHR* (Z)‐ 3 and 3‐amino‐1,2‐propadienylidene complexes L n MCCC(Ph)NHR* 4 [R* = 2,3,4,6‐tetra‐ O ‐pivaloyl‐β‐D‐galactopyranosyl] are obtained by the addition of galactopyranosylamine R*‐NH 2 2 to the corresponding alkynylcarbene complexes L n MC(OEt)CCPh 1 [L n M = (CO) 5 Cr, (CO) 5 W]. Treatment of (Z)‐ 3 with two equivalents of tert ‐butyl isocyanide ( 5 ) affords isocyanide complexes 6 and ketene imines 7. The latter cyclize spontaneously to give galactopyranosylpyrroles 8 which form stable atropisomers 8A and 8B.