References
1a
Snieckus V.
Chem. Rev.
1990,
90:
879
1b
Cuevas J.-C.
Patil P.
Snieckus V.
Tetrahedron
Lett.
1989,
30:
5841
2
Metallinos C.
Nerdinger S.
Snieckus V.
Org.
Lett.
1999,
1:
1183
3 More forcing conditions are required
to dealkylate N-t-Bu benzamides;
see: Reitz DB.
Massey SM.
J. Org. Chem.
1990,
55:
1375
4a Cumyl
amine can be prepared from cumyl alcohol by a modification of the
procedure of: Balderman D.
Kalir A.
Synthesis
1978,
24 .
The azide is reduced with LiAlH4 (Et2O/0 °C → r.t. → reflux)
or H2 (Lindlar’s catalyst/EtOH) instead of
Raney nickel
4b Cumyl amine is also
commercially available from TCI America: catalogue no. C1293.
5
Melnick M.
Reich SH.
Lewis KK.
Mitchell JLJ.
Nguyen D.
Trippe AJ.
Dawson H.
Davies JF.
Appelt K.
Wu B.
Musick L.
Gehlhaar DK.
Webber S.
Shetty B.
Kosa M.
Kahil D.
Andrada D.
J.
Med. Chem.
1996,
39:
2795
6
Charette AB.
Chua P.
Synlett
1998,
163
7 Ang, P. J. A.; Metallinos, C.; Snieckus,
V., unpublished results.
8
Chao W.
Weinreb SM.
Tetrahedron Lett.
2000,
41:
9199
9
Clayden J.
Menet CJ.
Mansfield DJ.
Org. Lett.
2000,
2:
4229
10
Clayden J.
Tchabanenko K.
Chem. Commun.
2000,
317
11
Metallinos C.
Ph.D.
Thesis
Queen’s University;
Kingston, Ontario,
Canada:
2001.
12
Tsukazaki M.
Tinkl M.
Roglans A.
Chapell BJ.
Taylor NJ.
Snieckus V.
J. Am.
Chem. Soc.
1996,
118:
685
13
Laufer RS.
Veith U.
Taylor NJ.
Snieckus V.
Org. Lett.
2000,
2:
629
14 Metallinos, C.; Szillat, H.; Taylor,
N. J.; Snieckus, V., manuscript in preparation.