TOJC:whiteside and organolithium
rossjm@plu.edu
Thu, 12 Dec 1996 21:20:18 -0800 (PST)
Allister
This question was brought up in the problem session today. From what
I understood from the discussion the use of organolithium reagents
should produces the same results as a Corey-Posner, Whitesides-House
synthesis, essentially the formation of a C-C bond. So I believe the
answer to your first question is yes. However, according to Dr.Fryhle,
the C-P, W-H synthesis is a difficult reaction to carry out. So though it
is a useful reaction, it is easier to use an organolithium. Furthermore,
since Mg is more reactive than Li and Grignard reagents are easier to
prepare than organolithium reagents, a Grignard reaction is the best way
to synthesize a C-C bond formation.
Hope this helps.
JM Ross
On Wed, 11 Dec 1996, Allister Stone wrote:
> Hi,
> Is it possible that after reacting organolithiulm reagents with adehyde or
> keytone to add CuI, RX to do a whiteside synthesis? What would yeilds be
> like and are there potential problems with doing this type of rxn if its
> possible?
>
> thanks,
> allister
> stoneag@plu.edu
>
>