Abstract
A mild and efficient procedure is described for the synthesis of amine-substituted diazoacetoacetates by the addition of ethyl 3-(tert-butyldimethylsilanoxy)-2-diazobut-3-enoate to aldimines catalysed by MgI2 etherate (MgI2•(OEt2)n) in MeCN. The reaction produces good to excellent yield at room temperature.
References
1.
Zhang Y.
, and
Wang J. B.
, Chem. Commun. , 2009 , 36 , 5350 .
2.
Davies H.M. L.
, and
Manning J. R.
, Nature , 2008 , 451 , 417 .
3.
Doyle M.P.
,
Ratnikov M.
, and
Liu Y.
, Org. Biomol. Chem. , 2011 , 9 , 4007 .
4.
Fang C.
,
Shanahan C. S.
,
Paull D. H.
, and
Martin S. F.
, Angew. Chem. Int. Ed. , 2012 , 45 , 10596 .
5.
Nicolaou K.C.
,
Ding H.
,
Richard J.
, and
Chen D. Y.
, J. Am. Chem. Soc. , 2010 , 7 , 1227 .
6.
Doyle M.P.
,
McKervey M. A.
, and
Ye T.
, Modern catalytic methods for organic synthesis with diazo compounds: from cyclopropanes to ylides , John Wiley and Sons , New York , 1998 .
7.
Doyle M.P.
,
Duffy R.
,
Ratnikov M. O.
, and
Zhou L.
, Chem. Rev. , 2010 , 110 , 704 .
8.
Merlic C.A.
, and
Zechman A. L.
, Synthesis , 2003 , 8 , 1137 .
9.
Davies H.M. L.
, and
Beckwith R. E. J.
, Chem. Rev. , 2003 , 103 , 2861 .
10.
Davies H.M. L.
, and
Antoulinakis E. G.
, Org. React. , 2001 , 57 , 1 .
11.
Hodgson D.M.
,
Pierard F. Y. T. M.
, and
Stupple P. A.
, Chem. Soc. Rev. , 2001 , 30 , 50 .
12.
Liu Y.
,
Zhang Y.
,
Jee N.
, and
Doyle M. P.
, Org. Lett. , 2005 , 7 , 5171 .
13.
Dong C.
,
Mo F.
, and
Wang J.
, J. Org. Chem. , 2008 , 73 , 1971 .
14.
Zhong T.J.
,
Wu T. P.
, and
Zhang X. X.
, J. Chem. Res. , 2014 , 38 , 690 .
15.
Arkley V.
,
Attenburrow J.
,
Gregory G. I.
, and
Walker T.
, J. Chem. Soc. , 1962 , 1260 .
16.
Deng Q.H.
,
Xu H. W.
,
Yuen A. W. H.
,
Xu Z. J.
, and
Che C. M.
, Org. Lett. , 2008 , 10 , 1529 .
