Abstract
An avenue to homotyrosinol derivatives through a Heck coupling
of 4-iodophenyl acetate with a vinylglycinol derivative required
extensive screening of catalysts and conditions. The use of Pd(OAc)2 and N -phenylurea as the ligand ultimately
provided excellent results.
Key words
coupling - Heck reaction - homotyrosine - palladium -
N -phenylurea
References
1a </A>
Ciufolini MA.
Braun NA.
Canesi S.
Ousmer M.
Chang J.
Chai D.
Synthesis
2007,
3759
1b </A>
Mendelsohn BA.
Ciufolini MA.
Org.
Lett.
2009,
11:
4736
1c </A>
Liang H.
Ciufolini MA.
1d </A>
Frie JL.
Jeffrey CS.
Sorensen EJ.
Org. Lett.
2009,
11:
5394
1e </A>
Sabot C.
Guerard KC.
Canesi S.
Chem.
Commun.
2009,
2941
<A NAME="RM01010SS-2">2 </A>
Canesi S.
Bouchu D.
Ciufolini MA.
Angew.
Chem. Int. Ed.
2004,
43:
4336
<A NAME="RM01010SS-3">3 </A>
Ca. $100/gram as
quoted in SciFinder.
<A NAME="RM01010SS-4">4 </A>
Suhartono M.
Weidlich M.
Stein T.
Karas M.
Dürner G.
Göbel MW.
Eur. J. Org.
Chem.
2008,
1608
5a </A>
Afzaliardakani A.
Rapoport H.
J. Org.
Chem.
1980,
45:
4817
5b </A>
Krebs A.
Ludwig V.
Prizer J.
Durner G.
Gobel MW.
Chem. Eur.
J.
2004,
10:
544
6a </A>
Heck RF.
Nolley JP.
J. Org. Chem.
1972,
37:
2320
6b </A>
Heck RF.
Org. React.
1989,
27:
345
6c </A>
Beletskaya I.
Cheprakov A.
Chem. Rev.
2000,
100:
3009
6d </A>
Littke AF.
Fu GC.
Angew.
Chem. Int. Ed.
2002,
41:
4176
6e </A>
Braese S.
de Meijere A.
Cross-coupling
of organic halides with alkenes: The Heck reaction , In Metal-Catalyzed Cross-Coupling Reactions
Diederich F.
Stang PJ.
Wiley-VCH;
Weinheim:
2004.
7a </A>
Grubbs RH.
Handbook
of Metathesis
Wiley-VCH;
Weinheim:
2003.
7b </A>
Grubbs RH.
Trnka TM.
Ruthenium-Catalyzed Olefin Metathesis , In Ruthenium in Organic Synthesis
Murahashi S.-I.
Wiley-VCH;
Germany:
2004.
7c </A>
Trnka TM.
Grubbs RH.
Acc.
Chem. Res.
2000,
34:
18
<A NAME="RM01010SS-8">8 </A> For a review, see:
Miyaura N.
Suzuki A.
Chem. Rev.
1995,
95:
2457
<A NAME="RM01010SS-9">9 </A>
Collier PN.
Campbell AD.
Patel I.
Raynham TM.
Taylor RJK.
J. Org. Chem.
2002,
67:
1802
10a </A>
Osborn JA.
Jardine FH.
Young JF.
Wilkinson G.
J. Chem. Soc. A
1966,
1711
10b </A>
Mannig D.
Noth H.
Angew. Chem. Int. Ed.
1985,
24:
878
11 </A>
There was no reaction in THF at temperatures
below 60 ˚C. At reflux, the substrate was converted
into complex mixtures of products.
<A NAME="RM01010SS-12">12 </A>
Scholl M.
Ding S.
Lee CW.
Grubbs RH.
Org. Lett.
1999,
1:
953
<A NAME="RM01010SS-13">13 </A>
Garber SB.
Kingsbury JS.
Gray BL.
Hoveyda AH.
J.
Am. Chem. Soc.
2000,
122:
8168
14a </A>
Schwab P.
France MB.
Ziller JW.
Grubbs RH.
Angew. Chem. Int. Ed.
1995,
34:
2039
14b </A>
Schwab P.
Grubbs RH.
Ziller JW.
J. Am. Chem. Soc.
1996,
118:
100
14c </A>
Kingsbury JS.
Harrity JPA.
Bonitatebus PJ.
Hoveyda AH.
J. Am. Chem. Soc.
1999,
121:
791
<A NAME="RM01010SS-15">15 </A>
Barder TE.
Walker SD.
Martinelli JR.
Buchwald SL.
J.
Am. Chem. Soc.
2005,
127:
4685
16a </A>
Cui X.
Zhou Y.
Wang N.
Liu L.
Guo QX.
Tetrahedron Lett.
2007,
48:
163
16b </A>
Cui X.
Li J.
Fu Y.
Liu L.
Guo QX.
Tetrahedron
Lett.
2008,
49:
3458
17a </A>
Dale JA.
Mosher HS.
J.
Am. Chem. Soc.
1973,
95:
512
17b </A> For a review, see:
Kusumi T.
Ooi T.
Ohkubo Y.
Yabuuchi T.
Bull. Chem. Soc. Jpn.
2006,
79:
965
<A NAME="RM01010SS-18">18 </A>
Battace A.
Zair T.
Doucet H.
Santelli M.
Synthesis
2006,
3495
