Abstract
The synthesis of the very first example of a thioacetal containing two camphor skeleta is described. The acetal was prepared by treating 10-mercapto-iso-borneol with camphorquinone and its stereochemistry confirmed by NMR spectroscopy and X-ray crystallography.
Keywords
References
1.
Oppoizer W.
, Tetrahedron , 1987 , 43 , 1969 .
2.
(a)
Oppolzer W.
, Pure Appl. Chem. , 1990 , 62 , 1241
3.
Oppolzer W.
, Angew. Chem., Int. Ed. Engl. , 1984 , 23 , 876 .
4.
(a)
McNulty J.
, and
Millar M. J.
, J Org. Chem. , 1999 , 64 , 5312
5.
Knollmuller M.
,
Ferencic M.
,
Gartner P.
,
Mereiter K.
, and
Noe C. R.
, Tetrahedron: Asymmetry , 1998 , 9 , 4009 .
6.
(a)
Eliel E.L.
,
Frazee W. J.
, J. Org. Chem. , 1979 ; 44 , 1598
7.
Lucchi O.D.
,
Lucchini V.
,
Marchioro C.
,
Valle G.
, and
Modena G.
J. Org. Chem. , 1986 , 51 , 1457 .
8.
Wiley J.
, Organic Syntheses Collective Vol 5 , 1973 , p. 196 .
9.
(a)
Kaye P.T.
,
Learmonth R. A.
, and
Ravindran S. S.
, Synth. Comun. , 1993 , 23 , 437
10.
Kaye P.T.
, and
Ravindran S. S.
, S. Afr. J. Chem. , 1994 , 47 , 17
11.
Kaye P.T.
, and
Ravindran S. S.
, S. Afr. J. Chem. , 1995 , 48 , 64 .
12.
Mugesh G.
,
Singh B.
, and
Butcher J.
, J Chem. Research(S) , 1999 , 472 .
13.
Delft N.B. V.
, COLLECT , The Netherlands , 2000 .
14.
DENZO 2.
Otwinowski Z.
, and
Minor W.
, Methods in Enzymologv , 276 , 307 –326 , 1997 .
15.
Sheldrick G.M.
, SHELXS-97 , University of Göttingen , Germany , 1997 .
16.
Spek A.L.
, PLATON , University of Utrecht , The Netherlands , 1997 .
