Abstract
Ring-closing metathesis (RCM) and intramolecular Horner–Wadsworth–Emmons (HWE) reactions were assessed for synthesis of cis-5-methyl-6-phenylethyl-5,6-dihydro-α-pyrone. The RCM reaction employing Grubbs’ second generation catalyst afforded a 96% yield at 80 °C in toluene. The HWE reaction under modified Masamune–Roush conditions delivered only 23% yield due to a competitive elimination reaction.
Keywords
References
1.
Kumar
P.
, and
Naidu
S. V.
, J. Org. Chem. , 2006 , 71 , 3935 .
2.
Hu
S.G.
,
Hu
T. S.
, and
Wu
Y. L.
, Org. Biomol. Chem. , 2004 , 2 , 2305 .
3.
Trost
B.M.
, and
Yeh
V. S. C.
, Org. Lett. , 2002 , 4 , 3513 .
4.
Chandrasekhar
M.
,
Chandra
K. L.
, and
Singh
V. K.
, J. Org. Chem. , 2002 , 68 , 4039 .
5.
Chandrasekhar
M.
,
Raina
S.
, and
Singh
V. K.
, Tetrahedron Lett. , 2000 , 41 , 4969 .
6.
Honda
T.
,
Horiuchi
S.
,
Misutani
H.
, and
Kanai
K.
, J. Org. Chem. , 1996 , 61 , 4944 .
7.
Keck
G.E.
,
Knutson
C. E.
, and
Wiles
S. A.
, Org. Lett. , 2001 , 3 , 707 .
8.
BouzBouz
S.
, and
Cossy
J.
, Org. Lett. , 2003 , 5 , 1995 .
9.
Ghadigoanokar
S.
,
Koli
M. R.
,
Gamre
S. S.
,
Choudhary
M. K.
,
Chattopadhyay
S.
, and
Sharma
A.
, Tetrahedron Asymmetry , 2012 , 23 , 1093 .
10.
You
Z.W.
,
Jiang
Z. X.
,
Wang
B. L.
, and
Qing
F. L.
, J. Org. Chem. , 2006 , 71 , 7261 .
11.
Wach
J.-Y.
,
Güttinger
S.
,
Kutay
U.
, and
Gademann
K.
, Bioorg. Med. Chem. Lett. , 2010 , 20 , 2843 .
12.
Fleury
E.
,
Sorin
G.
,
Prost
E.
,
Pancrazi
A.
,
Sautel
F.
,
Massiot
G.
,
Lannou
M.-I.
, and
Ardisson
J.
, J. Org. Chem. , 2013 , 78 , 855 .
13.
Shing
T.K. M.
, and
Aloui
M.
, J. Chem. Soc., Chem. Commun. , 1988 , 1526 .
14.
Ramesh
S.
, and
Franck
R. F.
, Tetrahedron Asymmetry , 1990 , 1 , 137 .
15.
Isobe
M.
,
Kitamura
M.
, and
Goto
T.
, Tetrahedron Lett. , 1979 , 20 , 3465 .
16.
Yang
F.
,
Feng
L.
,
Wang
N. Z.
,
Liu
X. G.
,
Li
J.
, and
Shen
Y. H.
, Tetrahedron , 2013 , 69 , 9463 .
17.
Kobayashi
S.
, and
Nishio
K.
, J. Org. Chem. , 1994 , 59 , 6620 .
18.Evans pKa table, http://evans.rc.fas.harvard.edu/pdf/evans_pKa_table.pdf.
19.
Guthrie
J.P.
, and
Cossar
J.
, Can. J. Chem. , 1986 , 64 , 2470 .
20.
Chen
X.M.
, and
Wiemer
D. F.
, J. Org. Chem. , 2003 , 68 , 6597 .
21.
Blanchette
M.A.
,
Choy
W.
,
Davis
J. T.
,
Essenfeld
A. P.
,
Masamune
S.
,
Roush
W. R.
, and
Sakai
T.
Tetrahedron Lett. , 1984 , 25 , 2183 .
