Abstract
Virtually diastereochemically pure 3-heterosubstituted isoindolinones have been obtained by nucleophilic addition on an N-acylhydrazonium salt generated by acidic treatment of the corresponding 3-hydroxy derivatives bearing a SMP type auxiliary and their structure has been assessed by single crystal X-ray analysis.
References
1.
Koenig B.
,
Leser U.
,
Schaefer W.
,
Zilch H.
,
Poll T.
,
Leinert H.
, and
Maertens A.
, Ger. Offen. DE 4103177 (1992 ); Chem. Abstr. , 1992, 117 , 212489.
2.
Iino T.
,
Sato Y.
,
Nishimura T.
,
Banba M.
,
Eiki J.
, and
Nagase T.
, Jpn. Kokai Tokkyo Koho JP 2002255967 (2002); Chem. Abstr. , 2002 , 137 , 232648 .
3.
(a)
Chen J.M.
,
Chen X.
,
Fardis M.
,
Jin H.
,
Kim C. U.
, and
Schacherer L. N.
, PCT Int. Appl. 2004035577 (2004); Chem. Abstr. , 2004, 140 , 375156; (b) PCT Int. Appl. 2004035576 (2004); Chem. Abstr. , 2004, 140 , 375155.
4.
Blanco-Pillado M.-J.
,
Chappell M. P.
,
Garcia de la Torre M.
,
Diaz Buezo N.
,
Fritz J. E.
,
Holloway W. G.
,
Matt J. E.
Jr.
,
Mitch C. H.
,
Pedregal-Tercero C.
,
Quimby S. J.
,
Siegel M. G.
,
Smith D. R.
,
Stucky R. D.
,
Takeuchi K.
,
Thomas E. M.
, and
Wolfe C. N.
, PCT Int. Appl. 20040401 (2004 ); Chem. Abstr. , 2004, 140 , 303538.
5.
Demerson C.A.
, and
Jirkovsky I. L.
, US Pat. US 4668687 (1987 ); Chem. Abstr. , 1983, 98 , 160738.
6.
Park J.S.
,
Kyong K. U.
,
Jae J. Y.
,
Yoo E. S.
,
Byun Y. S.
, and
Park M. H.
, Arch. Pharm. Res. , 2001 , 24 , 367 .
7.
Mertens A.
,
Zilch H.
,
Koenig B.
,
Schaefer W.
,
Poll T.
,
Kampe W.
,
Seidel H.
,
Leser U.
, and
Leinert H.
, J. Med. Chem. , 1993 , 36 , 2526 .
8.
Suzuki H.
,
Aoyagi S.
, and
Kibayashi C.
, J. Org. Chem. , 1995 , 60 , 6114 .
9.
Deniau E.
, and
Enders D.
, Tetrahedron Lett. , 2002 , 43 , 8055 .
10.
Deniau E.
,
Enders D.
,
Couture A.
, and
Grandclaudon P.
, Tetrahedron: Asymmetry , 2005 , 16 , 875 –881 .
11.
Sheldrick G.M.
, SHELXTL, Program for Crystal Structure Solution and Refinement , Bruker AXS Inc. , Madison, WI , 1997
