Abstract
Compared with tetrahydrofuran (THF) as a solvent for the addition reactions between Grignard reagents and carbonyl compounds 2-methyltetrahydrofuran affords the corresponding adducts in higher yields with higher chemoselectivities. Moreover, 2-methyltetrahydrofuran can be readily recycled and reused, which lowers the cost of the process and makes the reaction greener.
References
1.
Sheldon R.A.
, Green Chem. , 2005 , 7 , 267 .
2.
Wakefield B.J.
, Organomagnesium methods in organic chemistry , Academic Press : San Diego , 1995 .
3.
Aycock D.F.
, Org. Process Res. Dev. , 2007 , 11 , 156 .
4.
Robert T.
,
Velder J.
, and
Schmalz H.
, Angew. Chem. Int. Ed. , 2008 , 47 , 7718 .
5.
Hatano M.
,
Matsumura T.
, and
Ishihara K.
, Org. Lett. , 2005 , 7 , 573 .
6.
Finkam M.
, and
Akteries B.
, U.S. Patent 20050215821, 2005; Chem. Abstr. 2005 , 143 , 346904.
7.
Jones A.C.
,
Sanders A. W.
,
Bevan M. J.
, and
Reich H. J.
, J. Am. Chem. Soc. , 2007 , 129 , 3492 .
8.
Hatano M.
,
Miyamoto T.
, and
Ishihara K.
, J. Org. Chem. , 2006 , 71 , 6474 .
9.
Li N.
,
Yu S.
, and
Kabalka G. W.
, J. Organomet. Chem. , 1997 , 531 , 101 .
10.
Driver T.G.
,
Harris J. R.
, and
Woerpel K. A.
, J. Am. Chem. Soc. , 2007 , 129 , 3836 .
11.
Firouzabadi H.
,
Iranpoor N.
,
Hazarkhani H.
, and
Karimi B.
, Synth. Commun. , 2003 , 33 , 3653 .
12.
Bellesia F.
,
Ghelfi F.
,
Pagnoni U. M.
, and
Pinetti A.
, Gazz. Chim. Ital. , 1992 , 122 , 437 .
13.
Mukaiyama T.
,
Shintou T.
, and
Fukumoto K.
, J. Am. Chem. Soc. , 2003 , 125 , 10538 .
14.
Zhang W.
,
Liu J.
,
Xu G.
,
Yuan Q.
, and
Sayre L. M.
, Chem. Res. Toxicol. , 2003 , 16 , 512 .
15.
Coldham L.
,
Patel J. J.
,
Raimbault S.
,
Whittaker D. T. E.
,
Adams H.
,
Fang G. Y.
, and
Aggarwal V. K.
, Org. Lett , 2008 , 10 , 141 .
16.
Sundby E.
,
Andersen M. M.
,
Hoff B. H.
, and
Anthonsen T.
, ARKIVOC , 2001 , 10 , 76 .
17.
Imamoto T.
,
Kusumoto T.
,
Tawarayama Y.
,
Sugiura Y.
,
Mita T.
,
Hatanaka Y.
, and
Yokoyama M.
, J. Org. Chem. , 1984 , 49 , 3904 .
18.
Zarbin P.H. G.
,
Arrigoni E. D. B.
,
Reckziegel A.
,
Moreira J. A.
,
Baraldi P. T.
, and
Vieira P.C.
, J. Chem. Ecol. , 2003 , 29 , 377 .
19.
Wrobel J.
, and
Galuszko K.
, Tetrahedron Lett , 1965 , 49 , 4381 .
20.
Kato Y.
, and
Mase T.
, Tetrahedron Lett. , 1999 , 40 , 8823 –8826 .
21.
Tanaka S.
,
Saburi H.
,
Ishibashi Y.
, and
Kitamura M.
, Org. Lett. , 2004 , 6 , 1873 .
22.
Antunes C.S. A.
,
Bietti M.
,
Lanzalunga O.
, and
Salamone M.
, J. Org. Chem. , 2004 , 69 , 5281 .
23.
Li G.
, and
Zhao G.
, J. Org. Chem. , 2005 , 70 , 4272 –4278 .
24.
Liu L.
,
Tang L.
,
Yu L.
,
Chang W.
, and
Li J.
, Tetrahedron , 2005 , 61 , 10930 .
25.
Kuriyama M.
,
Shimazawa R.
, and
Shirai R.
, J. Org. Chem. , 2008 , 73 , 1597 .
26.
Ikeda H.
,
Namai H.
,
Taki H.
, and
Miyashi T.
, J. Org. Chem. , 2005 , 70 , 3806 .
27.
Martin-Matute B.
,
Nevado C.
,
Cardenas D. J.
, and
Echavarren A. M.
, J. Am. Chem. Soc. , 2003 , 125 , 5757 .
28.
Lehmann J.
, and
Marquardt N.
, Synthesis , 1987 , 1064 .
29.
Li L.
,
Cai P.
,
Guo Q.
, and
Xue S.
, J. Org. Chem. , 2008 , 73 , 3516 .
30.
Alvarado C.
,
Guzman A.
,
Diaz E.
, and
Patino R.
, J. Mex. Chem. Soc. , 2005 , 49 , 324 .