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1,3‐Diethynylallenes (DEAs): Enantioselective Synthesis, Absolute Configuration, and Chiral Induction in 1,1,4,4‐Tetracyanobuta‐1,3‐dienes (TCBDs)
Author(s) -
AlonsoGómez José Lorenzo,
Schanen Patrick,
RiveraFuentes Pablo,
Seiler Paul,
Diederich François
Publication year - 2008
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200801456
Subject(s) - enantioselective synthesis , absolute configuration , allene , yield (engineering) , chromophore , chemistry , optically active , sn2 reaction , stereochemistry , combinatorial chemistry , physics , organic chemistry , catalysis , thermodynamics
Optically active 1,3‐diethynylallenes (DEAs) were prepared by enantioselective Pd‐mediated S N 2′‐type cross‐coupling and their absolute configuration was determined by X‐ray analysis. Addition of tetracyanoethene (TCNE) to donor‐substituted DEAs affords novel 1,1,4,4‐tetracyanobutadiene (TCBDs)‐based charge‐transfer chromophores in high yield. CD spectroscopy reveals strong chiral induction from the optically pure allene into the directly adjacent TCBD moieties.