Synthetic
organic chemistry is a fascinating and vital area of
modern chemistry. It produces a funny adventure since
it offers intellectual excitement and challenges, and
one can create a new universe by doing synthetic organic
chemistry. Furthermore, it will constitute the first
step for the creation of novel medicines.
Although synthetic organic chemistry
has now rapidly progressed, yet how inferior are our
methods compared with those of the life process. Thus,
exploitation of new methods and new reagents in addition
to new principles of organic synthesis are needed. Our
research interests focus on exploitation of new methods
and new reagents in organic synthesis and we have already
developed several versatile synthetic reagents, eg.,
trimethylsilyldiazomethane (Me3SiCHN2) and trimethylsilylketene
(Me3SiCH=C=O). Additionally, Organic syntheses aiming
at the recent demands such as social contribution, atom-economy
and safety, have been aggressively studied. |
(1) Synthetic
applications of Me3SiCHN2 and Me3SiCH=C=O: Me3SiCHN2
is a stable and safe substitute for hazardous diazomethane
and acts as a C1-unit introducer and a [C-N-N]azole
synthon. Moreover, Me3SiCHN2 can be used for the generation
of alkylidenecarbene species from carbonyl compounds.
Meanwhile, Me3SiCH=C=O is a stable and safe substitute
for hazardous ketene, as a building block for heterocycles.
[Tetrahedron Lett. 2006, 47, 1137 and Tetrahedron Lett.
2007, 48, 7019]
(2) Asymmetric Ni-catalyzed arylation
and allylation of carbonyl and imino compounds: The
reaction is one of the most important C-C bond-forming
reactions, because chiral sec-methanols are important
intermediates for the synthesis of biologically active
compounds. From the viewpoint of cost and practical
convenience, we have focused on the use of a much cheaper
and more naturally abundant metal catalyst, Ni, than
Rh and Pd in order to develop the title reactions. [Tetrahedron
Lett. 2007, 48, 4115]
(3) Chiral hemilabile phosphine
or N-heterocyclic carbene ligands: We have developed
new hemilabile phosphine ligands with both soft and
hard coordinated centers within one molecule, and carbene
ligands mimicking chiral center in which a chiral carbon
center induces a preferred conformation, which is fixed
by formation of a chelate structure with metal. [Synthesis
2006, 3809 and Tetrahedron Lett. 2006, 47, 1417]
(4) Construction of tetra-substituted
carbon by organocatalyst: We have developed new methods
for cyanation reaction, etc of lower reactive ketones
and ketimines than aldehydes and aldimines in the presence
of a organocatalyst. [Synthesis 2006, 2649] |