Abstract
The Evans-Chan-Lam variant of the Ullman condensation
has been explored to deliver O-arylated tyrosines and tyrosinyl peptides.
Key modifications for success were the slow addition of boronic
acids to the phenol-catalyst mixture. Selectivity and scope are
investigated.
Key words
bioorganic chemistry - copper - cross coupling - peptides - phenols
References and Notes
1 Feliu L.
Planas M.
Int. J. Pept. Res. Ther.
2005,
11:
53
2 Kahne D.
Leimkuhler C.
Wei L.
Walsh C.
Chem. Rev.
2005,
105:
425
3 Waldmann H.
He Y.-P.
Tan H.
Arve L.
Arndt H.-D.
Chem. Commun.
2008,
5562
4 Itokawa H.
Takeya K.
Heterocycles
1993,
35:
1467
5 Frlan R.
Kikelj D.
Synthesis
2006,
2271
6 Nishiyama S.
Nakamura K.
Suzuki Y.
Yamamura S.
Tetrahedron Lett.
1986,
27:
4481
7 Boger DL.
Zhou J.
J. Org. Chem.
1996,
61:
3938
8a Olivera R.
SanMartin R.
Churruca F.
Domínguez E.
J.
Org. Chem.
2002,
67:
7215
8b Cai Q.
Zou B.
Ma D.
Angew.
Chem. Int. Ed.
2006,
45:
1276
8c Cai Q.
He G.
Ma D.
J.
Org. Chem.
2006,
71:
5268
9 Chapman CJ.
Matsuno A.
Frost CG.
Willis MC.
Chem. Commun.
2007,
3903
10a Chan DMT.
Monaco KL.
Wang R.-P.
Winters
MP.
Tetrahedron Lett.
1998,
39:
2933
10b Evans DA.
Katz JL.
West TR.
Tetrahedron Lett.
1998,
39:
2937
10c Lam PYS.
Clark GC.
Saubern S.
Adams J.
Winters MP.
Chan DMT.
Combs A.
Tetrahedron Lett.
1998,
39:
2941
10d Ley SV.
Thomas AW.
Angew.
Chem. Int. Ed.
2003,
42:
5400
10e Chan DMT.
Lam PYS. In Boronic Acids
Hall D.
Wiley-VCH;
Weinheim:
2005.
p.205
11a Evans DA.
Katz JL.
Peterson GS.
Hintermann T.
J.
Am. Chem. Soc.
2001,
123:
12411
11b Deng H.
Jung
JK.
Liu T.
Kuntz KW.
Snapper ML.
Hoveyda
AH.
J.
Am. Chem. Soc.
2003,
125:
9032
11c Shinohara T.
Deng H.
Snapper ML.
Hoveyda AH.
J. Am. Chem. Soc.
2005,
127:
7334
12 Hitotsuyanagi Y.
Ishikawa H.
Naito S.
Takeya K.
Tetrahedron Lett.
2003,
44:
5901
13 Lam PYS.
Vincent G.
Clark CG.
Deudon S.
Jadhav PK.
Tetrahedron Lett.
2001,
42:
3415
14 All peptides were accessed by standard
solid-phase peptide synthesis protocols on 2-Cl-trityl or Rink-amide
resins, when appropriate, using Fmoc-protected amino acids and HOBt,
HBTU, and EtN(i -Pr)2 as coupling
reagents.
15 Chiarello J.
Joullie MM.
Synth. Commun.
1988,
18:
2211
16 Aurelio L.
Brownlee RTC.
Hughes AB.
Chem. Rev.
2004,
104:
5823
17 Olsen RK.
J.
Org. Chem.
1970,
35:
1912
18 Ishiyama T.
Murata M.
Miyaura N.
J.
Org. Chem.
1995,
60:
7508
19 Falck JR.
Bondlela M.
Ventkatamaran SK.
Srinivas D.
J. Org.
Chem.
2001,
66:
7148
