Abstract
In a process analogous to use of the Mukaiyama reagent, ω-hydroxyalkyl 2-pyridyl ester derivatives were converted into lactones by N-alkylation or the coordination of copper(II) triflate and transacylation of the resultant electrophilic ω-hydroxyalkanecarboxypyridinium salts.
Key words
lactonization - 2-pyridyl ester - copper(II) triflate - tetrahydroquinolizinone
References
1a
Corey EJ.
Nicolaou KC.
J. Am. Chem. Soc.
1974,
96:
5614
1b
Masamune S.
Kamata S.
Schilling W.
J. Am. Chem. Soc.
1975,
97:
3515
1c
Inanaga J.
Hirata K.
Saeki H.
Tatsuki T.
Yamaguchi M.
Bull. Chem. Soc. Jpn.
1979,
52:
1989
1d
Boden EP.
Keck GE.
J. Org. Chem.
1985,
50:
2394
1e
Steliou K.
Szczygielska-Nowosielska A.
Favre A.
Poupart MA.
Hanessian S.
J. Am. Chem. Soc.
1980,
102:
7578
1f
Boeckman RK.
Pruitt JR.
J. Am. Chem. Soc.
1989,
111:
8286
1g
Trost BM.
Chisholm JD.
Org. Lett.
2002,
4:
3743
2
Mukaiyama T.
Usui M.
Saigo K.
Chem. Lett.
1976,
49
3 For an example of macrolactonisation using solid-supported DCC, see: Keck GE.
Sanchez C.
Wager CA.
Tetrahedron Lett.
2000,
41:
8673
4a For the conversion of 6-(2,2′-bipyridyl) esters into amides with Zn(II), Co(II) or Ni(II) catalysis see: Propst RM.
Trzupek LS.
J. Am. Chem. Soc.
1981,
103:
3233
4b For the transesterification of 6-(2,2′-bipyridyl)esters and alcohols catalysed by CsF, see: Mukaiyama T.
Pai F.-C.
Onaka M.
Narasaka K.
Chem. Lett.
1980,
563
For the macrolactonization of hydroxyacids by reflux of their 6-phenyl-2-pyridyl esters and 4-toluenesulfonic acid in CH2 Cl2 see:
4c
Narasaka K.
Yamaguchi M.
Mukaiyama T.
Chem. Lett.
1977,
959
4d
Mukaiyama T.
Narasaka K.
Kikuchi K.
Chem. Lett.
1977,
441
4e For the conversion of 2-pyridyl thioesters into esters using silver(I) salts, see: Gerlach H.
Thalmann A.
Helv. Chim. Acta
1974,
57:
2661
4f For the use of related thioesters with CuBr2 activation for the synthesis of cyclic oligo-(R )-3-hydroxybutanoic esters, see: Lengweiler UD.
Fritz MG.
Seebach D.
Helv. Chim. Acta
1996,
79:
670
5a
Mootoo DR.
Konradsson P.
Udodong U.
FraserReid B.
J. Am. Chem. Soc.
1988,
110:
5583
5b
Mootoo DR.
Date V.
Fraser-Reid B.
J. Am. Chem. Soc.
1988,
110:
2662
5c
Fraser-Reid B.
Wu Z.
Udodong UE.
Ottosson H.
J. Org. Chem.
1990,
55:
6068
5d
Fraser-Reid B.
Udodong UE.
Wu Z.
Ottosson H.
Merritt JR.
Rao CS.
Roberts C.
Madsen R.
Synlett
1992,
927
6a For a review, see: van Maarseveen JH.
Comb. Chem. High Throughput Screening
1998,
1:
185
For additional examples, see:
6b
Nicolaou KC.
Roschangar F.
Vourloumis D.
Angew. Chem., Int. Ed. Engl.
1998,
37:
2014
6c
Nicolaou KC.
Winssinger N.
Pastor J.
Murphy F.
Angew. Chem., Int. Ed. Engl.
1998,
37:
2534
6d
Nicolaou KC.
Pastor J.
Winssinger N.
Murphy F.
J. Am. Chem. Soc.
1998,
120:
5132
7
Rastetter WH.
Phillion DP.
J. Org. Chem.
1981,
46:
3209
8 Sample identical (TLC, 1 H and 13 C NMR, GC-MS) with a commercial sample.
9a For a related alkylation using a triflate, see: Bates RB.
Taylor SR.
J. Org. Chem.
1993,
58:
4469
9b Prepared from the addition of Tf2 O to the corresponding alcohol and anhyd PVP in CH2 Cl2 at -78 °C (85%) and used directly without purification: McDougal PG.
Rico JG.
Oh YI.
Condon BD.
J. Org. Chem.
1986,
51:
3388
10
Graham RJ.
Weiler L.
Tetrahedron Lett.
1991,
32:
1027
11
Cooper MS.
Heaney H.
Newbold AJ.
Sanderson WR.
Synlett
1990,
533
12 PyClU = N ,N ,N′ ,N′ -bis(tetramethylene)chloroform-amidinium hexafluorophosphate. See: Coste J.
Frérot E.
Jouin P.
Tetrahedron Lett.
1991,
32:
1967
13
Kirkland TA.
Grubbs RH.
J. Org. Chem.
1997,
62:
7310
14 Sample identical (TLC, 1 H and 13 C NMR, GCMS) with the lactone intermediate in the synthesis of 24 .