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Enantioselective Diels−Alder Reactions of Optically Active (Buta‐1,3‐dien‐2‐yl)(salen)cobalt(III) Complexes
Author(s) -
Chapman John J.,
Day Cynthia S.,
Welker Mark E.
Publication year - 2001
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 - 10.1002/1099-0690(200106)2001:12<2273::aid-ejoc2273>3.0.co;2-i
Subject(s) - chemistry , cobalt , cyclohexene , enantioselective synthesis , diels–alder reaction , optically active , sodium borohydride , medicinal chemistry , organic chemistry , catalysis
The syntheses of two optically active (buta‐1,3‐dien‐2‐yl)(salen)Co complexes are reported. These dienyl complexes undergo Diels−Alder reactions with high enantioselectivity with a variety of dienophiles. One of the (salen)Co‐substituted Diels−Alder cycloadducts was characterized by X‐ray crystallography. A highlight of this chemistry is that the Diels−Alder cycloadduct containing cobalt complexes were cleanly cleaved at the cobalt−carbon bond with sodium borohydride in ethanol with concomitant optically active cobalt complex starting material and optically active cyclohexene cycloadduct recovery.