Abstract
The present work describes the synthesis of α-(2-trimethylstannyl)allyl
ketones via the palladium-catalyzed decarboxylative allylation of
cyclic (2-trimethylstannyl)allyl carboxylates. An example of the
synthetic potential for forming polycyclic systems using this methodology
is discussed.
Key words
decarboxylative allylation - palladium catalysis - spiro compounds - tin - transesterification
References <A NAME="RM83911-1">1 </A>
Current address: Nutek, S.A. de C.V.,
Div. Proyectos Especiales, Av. Agave No.102, Col. Barrio de Santa
Clara, Parque Industrial del Valle de Tehuacan, Santiago Miahuatlán,
Pue., México; drmiguelromero@yahoo.ca.
<A NAME="RM83911-2A">2a </A>
Weaver JD.
Recio A.
Grenning AJ.
Tunge JA.
Chem. Rev.
2011,
111:
1846
<A NAME="RM83911-2B">2b </A>
Heck RF. In Palladium Reagents
in Organic Synthesis , Best Synthetic
Methods
Katritzky AR.
Meth-Cohn O.
Rees CW.
Academic Press;
New York:
1990.
p.43-48
<A NAME="RM83911-2C">2c </A>
Tsuji J.
Takahashi H.
Morikawa M.
Tetrahedron
Lett.
1965,
4387
<A NAME="RM83911-2D">2d </A>
Trost BM.
Acc.
Chem. Res.
1980,
13:
385
<A NAME="RM83911-2E">2e </A>
Tsuji J.
Organic Synthesis with Palladium Compounds
Springer-Verlag;
New
York:
1980.
<A NAME="RM83911-2F">2f </A>
Trost BM. In Stereochemistry
of Organic and Bioorganic Transformations
Bartmann W.
Sharpless KB.
VCH;
New
York:
1986.
<A NAME="RM83911-2G">2g </A>
Trost BM.
Pure
Appl. Chem.
1981,
53:
2357
<A NAME="RM83911-2H">2h </A>
Trost BM.
Verhoeven TR. In Comprehensive Organometallic Chemistry
Vol.
8:
Wilkinson G.
Pergamon
Press;
Oxford:
1982.
Chap. 57.
<A NAME="RM83911-2I">2i </A>
Tsuji J.
Pure
Appl. Chem.
1982,
54:
197
<A NAME="RM83911-2J">2j </A>
Tsuji J.
Tetrahedron
1986,
42:
4361
<A NAME="RM83911-2K">2k </A>
Trost BM.
Chemtracts: Org.
Chem.
1988,
1:
415
<A NAME="RM83911-2L">2l </A>
Trost BM.
Angew.
Chem., Int. Ed. Engl.
1989,
28:
1173
<A NAME="RM83911-2M">2m </A>
Trost BM.
ACS
Adv. Chem.
1992,
230:
463
<A NAME="RM83911-3A">3a </A>
Carroll MF.
J. Chem. Soc.
1940,
1226
<A NAME="RM83911-3B">3b </A>
Kimel W.
Cope AC.
J. Am. Chem. Soc.
1943,
65:
1992
<A NAME="RM83911-3C">3c </A>
Wilson SR.
Price MF.
J.
Org. Chem.
1984,
49:
722
<A NAME="RM83911-4A">4a </A>
Tsuji J.
Yamada T.
Minami I.
Yuhara M.
Nisar M.
Shimizu I.
J. Org. Chem.
1987,
52:
2988
<A NAME="RM83911-4B">4b </A>
Tsuji J. In Handbook of Organopalladium Chemistry in Organic Synthesis
Vol.
2:
Negishi E.-i.
Meijere A.
Wiley;
New York:
2002.
p.1669
<A NAME="RM83911-5A">5a </A>
Atkins KE.
Walker WE.
Manyik RM.
Tetrahedron Lett.
1970,
3821
<A NAME="RM83911-5B">5b </A>
Trost BM.
Fullerton TJ.
J. Am. Chem. Soc.
1973,
95:
292
<A NAME="RM83911-5C">5c </A>
Tsuji J.
Pure
Appl. Chem.
1999,
71:
1539
<A NAME="RM83911-5D">5d </A>
Tsuji J.
New
J. Chem.
2000,
24:
127
<A NAME="RM83911-5E">5e </A>
Trost BM.
Chem.
Pharm. Bull.
2002,
50:
1
<A NAME="RM83911-5F">5f </A>
Graening T.
Schmalz H.-G.
Angew. Chem. Int. Ed.
2003,
42:
2580
<A NAME="RM83911-5G">5g </A>
Trost BM.
Hung MH.
J. Am. Chem. Soc.
1984,
106:
6837
<A NAME="RM83911-6A">6a </A>
Piers E.
Kaller AM.
Synlett
1996,
549
<A NAME="RM83911-6B">6b </A>
Piers E.
Kaller AM.
Tetrahedron Lett.
1996,
37:
5857
<A NAME="RM83911-6C">6c </A>
Kaller AM.
Ph.D. Thesis
University
of British Columbia;
Canada:
1997.
<A NAME="RM83911-7">7 </A>
Taber DF.
Amedio JC.
Patel YK.
J. Org. Chem.
1985,
50:
3618
<A NAME="RM83911-8">8 </A>
Alderice M.
Sum FW.
Weiler L.
Org.
Synth.
1984,
62:
14
<A NAME="RM83911-9">9 </A>
Piers E.
Romero MA.
Walker SD.
Synlett
1999,
1082
<A NAME="RM83911-10">10 </A>
Tsuji J.
Pure
Appl. Chem.
1986,
58:
869
<A NAME="RM83911-11">11 </A>
Piers E.
Romero MA.
J. Am. Chem. Soc.
1996,
118:
1215