Re: ORGLIST: 1-Carboxy-2-amino-cyclopropanes.

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From: Jonas Nilsson (jonni$##$ifm.liu.se)
Date: Mon May 07 2001 - 02:02:56 EDT


Does this have anything at all to do with the subject, or with any organic
chemistry at all?

NO!!

Please use your discression, and don't make this list an advertizing board.
We've got the rest of the internet working as thus.
Please use relevant subject.
/jN

----------///|||+X+|||\\\------------
      Jonas Nilsson
IFM, Dept. of Chemistry
  Linkoping University
    581 83 Linkoping
           Sweden

 phone: +46-13-285690
 fax: +46-13-281399
----------\\\|||+X+|||///------------


----- Original Message -----
From: "Dr.S.L.Gargh" <chemjyot$##$sancharnet.in>
To: "Jonas Nilsson" <jonni$##$ifm.liu.se>
Sent: Saturday, May 05, 2001 8:24 PM
Subject: Re: ORGLIST: 1-Carboxy-2-amino-cyclopropanes.


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> ----- Original Message -----
> From: "Jonas Nilsson" <jonni$##$ifm.liu.se>
> To: "Multiple recipients of list orglist" <orglist$##$dq.fct.unl.pt>
> Sent: Wednesday, May 02, 2001 7:24 PM
> Subject: ORGLIST: 1-Carboxy-2-amino-cyclopropanes.
>
>
> > Dear Readers.
> > I'm having trouble converting the dimethyl
1R,2R-cyclopropanedicarboxylate
> > to the methyl 1R-amino-2R-cyclopropanecarboxylate.
> >
> > |> = cyclopropane
> >
> > MeOOC-|>-COOMe -> MeOOC-|>-COOH This works fine!
> > MeOOC-|>-COOH -> MeOOC-|>-CNO (Using DPPA / Et3N) No
> > problems here!
> > MeOOC-|>-CNO -> MeOOC-|>-NHCOOR Works nice with any
> > alcohol I've tried
> >
> > Now to the hard part:
> > MeOOC-|>-CNO -> MeOOC-|>-NH3+ (Using HCl(aq or MeOH))
> > Doesn't work
> > MeOOC-|>-CNO -> MeOOC-|>-NH2 (Using H2O) Doesn't work
> > MeOOC-|>-NHCOOR -> MeOOC-|>-NH2 (Different
> deprotection
> > strategies) Doesn't work
> >
> > I've used different carbamates (FMOC, BOC, CBZ, Me, Ph) and different
> > deprotection strategies, but all seem to fail. It's hard for me to
> conclude
> > what happens, but I think the ring breaks up.
> >
> > I've searched the crossfire database for reactions, and there are a lot
of
> > compounds with a 1-carbonyl-2-(NH-prot.group.) substituted ring. There
are
> > also a lot of reactions invovling 1-(free amine) and a 2-aryl/alkyl
> > substituent pattern. But I get no hits with 1-(free amine) 2-(electron
> > withdrawing group). Are these compounds impossible to make or what?
> >
> > I later on need to derivitize both amine and carboxylate as amide bonds.
> > Will I have to do something like this do you think?
> >
> > MeOOC-|>-NHCOOR (DIBAL)-> HOCH2-|>-NHCOOR (Deprot,
coupling)->
> > HOCH2-|>-NHCOR' (ox., coupling) -> R''NOC-|>-NHCOR'
> >
> > Any other suggestions?
> > Please advise.
> > /jN
> > --
> >
> > ----------///|||+X+|||\\\------------
> > Jonas Nilsson
> > IFM, Dept. of Chemistry
> > Linkoping University
> > 581 83 Linkoping
> > Sweden
> >
> > phone: +46-13-285690
> > fax: +46-13-281399
> > ----------\\\|||+X+|||///------------
> >
>
>


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