Abstract
The development of DABCO-catalysed Michael addition of phenols and alcohols to ethyl 2,3-butadienoate provides an efficient synthetic pathway to (E)-β-aryloxyl and alkyloxyl acrylates in i-PrOH or under solvent-free conditions. The major advantages of the present method are wide substrate scope, mild reaction conditions, high stereoselectivity, and good reaction yields.
References
1.
Saito A.
,
Konishi T.
, and
Hanzawa Y.
, Org. Lett. , 2010 , 12 , 372 .
2.
Liu Y.
,
Wang H.
, and
Wan J. P.
, Org. Chem. , 2014 , 79 , 10599 .
3.
Zhu J.B.
,
Wang P.
,
Liao S.
, and
Tang Y.
, Org. Lett. , 2013 , 15 , 3054 .
4.
Li C.
,
Zhang Y.
,
Li P.
, and
Wang L.
, J. Org. Chem. , 2011 , 76 , 4692 .
5.
Fan Y.C.
, and
Kwon O.
, Org. Lett. , 2012 , 14 , 3264 .
6.
Stoermer M.J.
, and
Fairlie D. P.
, Aust. J. Chem. , 1995 , 48 , 677 .
7.
Moore J.L.
,
Kerr M. S.
, and
Rovis T.
, Tetrahedron , 2006 , 62 , 11477 .
8.
Kerr M.S.
, and
Rovis T.
, J. Am. Chem. Soc. , 2004 , 126 , 8876 .
9.
Stewart G.W.
,
Shevlin M.
,
Yamagata A. D. G.
,
Gibson A. W.
,
Keen S. P.
, and
Scott J. P.
, Org. Lett. , 2012 , 6 , 5440 .
10.
Sarrafi Y.
,
Sadatshahabi M.
,
Alimohammadi K.
, and
Tajbakhsh M.
, Green Chem. , 2011 , 13 , 2851 .
11.
Fan M.J.
,
Li G. Q.
,
Li L. H.
,
Yang S. D.
, and
Liang Y. M.
, Synthesis , 2006 , 2286 .
12.
Inanaga J.
,
Baba Y.
, and
Hanamoto T.
, Chem. Lett. , 1993 , 241 .
13.
Midland M.M.
, and
Koops R. W.
, J. Org. Chem. , 1990 , 55 , 5058 .
14.
Xu Z.F.
,
Cai C. X.
,
Jiang M.
, and
Liu J. T.
, Org. Lett. , 2014 , 16 , 3436 .
15.
Ma D.
,
Cai Q.
, and
Xie X.
, Synlett , 2005 , 1767 .
16.
Zhang Y.
,
Liu Y.
, and
Wan J. P.
, New J. Chem. , 2015 , 39 , 1567 .
17.
Wang Z.
,
Xu X.
, and
Kwon O.
, Chem. Soc. Rev. , 2014 , 43 , 2927 .
18.
Pei C.K.
, and
Shi M.
, Chem. Eur. J. , 2012 , 18 , 6712 .
19.
Cowen B.J.
, and
Miller S. J.
, Chem. Soc. Rev. , 2009 , 38 , 3102 .
20.
Wang T.
,
Hoon D. L.
, and
Lu Y.
, Chem. Commun. , 2015 , 51 , 10186 .
21.
Wang T.
,
Yu Z.
,
Hoon D. L.
,
Huang K.-W.
,
Lan Y.
, and
Lu Y.
, Chem. Sci. , 2015 , 6 , 4912 .
22.
Meng X.
,
Huang Y.
, and
Chen R.
, Org. Lett. , 2009 , 11 , 137 .
23.
Shi Y.L.
, and
Shi M.
, Org. Lett. , 2005 , 7 , 3057 .
24.
Kryshtal G.V.
,
Zhdankina G. M.
, and
Zlotin S. G.
, Mendeleev Commun. , 2002 , 12 , 57 .
25.
Guibe F.
,
Sarthou P.
, and
Bram G.
, Tetrahedron , 1974 , 30 , 3139 .