Abstract
A convenient procedure for the synthesis of cyanohydrins by the addition of trimethylsilyl cyanide to aromatic aldehydes, heteroaromatic aldehydes, aliphatic aldehydes and unsaturated aldehydes catalysed by MgI2 etherate (MgI2·(OEt2)n) in good to excellent yields is described.
References
1.
Gregory R.J.H.
, Chem. Rev. , 1999 , 99 , 3649 .
2.
North M.
, Synlett , 1993 , 807 .
3.
Evans D.A.
, and
Truesdale L.K.
, Tetrahedron Lett. , 1973 , 4929 .
4.
Reetz M. T.
,
Drewes M.W.
,
Harms K.
, and
Reif W.
, Tetrahedron Lett. , 1988 , 29 , 3295 .
5.
Komatsu N.
,
Uda M.
,
Suzuki H.
,
Takahashi T.
,
Domae T.
, and
Wada M.
, Tetrahedron Lett. , 1997 , 38 , 7215 .
6.
Bandini M.
,
Cozzi P.G.
,
Garelli A.
,
Melchiorrea P.
, and
Unami-Ronchi A.
, Eur. J. Org. Chem. , 2002 , 3243 .
7.
Vougioukas A.E.
, and
Kagan H.B.
, Tetrahedron Lett. , 1987 , 28 , 5513 .
8.
Whitesell J.K.
, and
Apodaca R.
, Tetrahedron Lett. , 1996 , 37 , 2525 .
9.
Evans D.A.
,
Truesdale L.K.
, and
Carroll G.L.
, J. Chem. Soc., Chem. Commun. , 1973 , 55 .
10.
Kurono N.
, and
Yamag M.
, J. Org. Chem. , 2005 , 70 , 6530 .
11.
Shibasaki M.
,
Kanai M.
, and
Funabashi K.
, Chem. Commun. , 2002 , 1989 .
12.
Ryu D.H.
, and
Corey E.J.
, J. Am. Chem. Soc. , 2004 , 126 , 8106 .
13.
Zhang X.
, and
Li W.
, Chin. J. Org. Chem. , 2003 , 23 , 1185 .
14.
Zhang X.
, Synlett , 2008 , 65 .
15.
Zhang X.
, and
Shi J.
, Tetrahedron , 2011 , 67 , 898 .
16.
Arkley V.
,
Attenburrow J.
,
Gregory G.I.
, and
Walker T.
, J. Chem. Soc. , 1962 , 1260 .
17.
Wen Y.
,
Ren W.
, and
Lu X.
, Chin. Chem. Lett. , 2011 , 22 , 1285 .
18.
Chu C.
,
Hsu C.
,
Lo P.
, and
Uang B.
, Tetrahedron: Asymmetry , 2011 , 22 , 1981 .
19.
North M.
,
Omedes-Pujol M.
, and
Williamson C.
, Chem.-A Eur. J. , 2010 , 16 , 11367 .
20.
Xu Q.
,
Xie Y.
,
Geng X.
, and
Chen P.
, Tetrahedron , 2010 , 66 , 624 .
21.
Kim Y.
,
Kim K.
,
Park S.
, and
Kim J.
, Tetrahedron Lett. , 2011 , 52 , 1378 .
22.
Sakthivel S.
, and
Punniyamurthy T.
, Tetrahedron: Asymmetry , 2010 , 21 , 2834 .
23.
Wen Y.
,
Ren W.
, and
Lu X.
, Org. Biomol. Chem. , 2011 , 9 , 6323 .
24.
Kuwazuka T.
,
Tanaka Y.
,
Kono T.
,
Watanabe S.
, and
Ishikawa K.
, JP02009874 (1990 ).