Lanthanum Trichloride: A Simple and Efficient Catalyst for Allylation of Aldehydes with Allyltributylstannane

REFERENCES

• (a) Yamamoto , Y. Acyclic stereocontrol via allylic organometallic compounds . Acc. Chem. Res. 1987 , 20 , 243 – 249 ; (b) Hoenberer , K. R. ; Hamblet , C. L. ; Leighton , J. L. Total synthesis of Leucascandrolide A . J. Am. Chem. Soc. 2000 , 122 , 12894 – 12895 ; (c) Nicolaou , K. C. ; Khim , D. W. ; Baati , R. Stereocontrolled total synthesis of apicularen A and its ΔZ isomer . Angew. Chem. Int. Ed. 2002 , 41 , 3701 – 3704 ; (d) Felphin , F. X. ; Lebreton , J. A highly stereoselective asymmetric synthesis of (−)-lobeline and (−)-sedamine . J. Org. Chem. 2002 , 67 , 9192 – 9199 .
   Web of Science ®Google Scholar
• (a) Yamamoto , Y. ; Asao , N. Selective reactions using allylic metals . Chem. Rev. 1993 , 93 , 2207 – 2293 ; (b) Narsaiah , A. V. ; Reddy , A. R. ; Rao , Y. G. ; Kumar , E. V. ; Prakasham , R. S. ; Reddy , B. V. S. ; Yadav , J. S. Mg-CdCl2, a bimetallic catalyst system for allylation of aldehydes with allylbromide: An efficient protocol for the synthesis of homoallylic alcohols . Synthesis 2008 , 3461 – 3464 .
   Web of Science ®Google Scholar
• (a) Nishigaichi , Y. ; Takuwa , A. ; Narula , Y. ; Maruyama , K. Versatile roles of Lewis acids in the reactions of allylic tin compounds . Tetrahedron 1993 , 49 , 7395 – 7426 ; (b) Marshal , J. A. Chiral allylic and allenic stannanes as reagents for asymmetric synthesis . Chem. Rev. 1996 , 96 , 31 – 48 .
   Web of Science ®Google Scholar
• (a) Konig , K. ; Neumann , W. P. Einige grignard-analoge reaktionen der C-Sn-bindung. Tetrahedron Lett. 1967, 23, 493–498; (b) Andrade , C. K. Z. ; Azevedo , N. R. ; Oliveira , G. R. NbCl5: A novel Lewis acid in allylation reaction. Synthesis 2002, 928–936; (c) Jin , Y. Z. ; Yasuda , N. ; Furuno , H. ; Inanaga , J. Organic synthesis in solid media: Silica gel as an effective and reusable medium for the selective allylation of aldehydes with tetraallyltin. Tetrahedron Lett. 2003, 44, 8765–8768.
   Google Scholar
• (a) Bartoli , G. ; Bosco , M. ; Giuliani , A. ; Marcantoni , E. ; Palmieri , A. ; Petrini , M. ; Sambri , L. Investigation into the allylation reactions of aldehydes promoted by the CeCl3·7H2O-NaI system as a Lewis acid . J. Org. Chem. 2004 , 69 , 1290 – 1297 ; (b) Li , G. L. ; Zhao , G. Efficient allylation of aldehydes promoted by carboxylic acids . J. Org. Chem. 2005 , 70 , 4272 – 4278 .
   PubMed Web of Science ®Google Scholar
• (a) Nishiyama , Y. ; Kakushou , F. ; Sonoda , N. Rhenium complex–catalyzed allylation of aldehydes with allyltributylstannane . Tetrahedron Lett. 2005 , 46 , 787 – 789 ; (b) Lingaiah , B. V. ; Ezikiel , G. ; Yakaiah , T. ; Reddy , G. V. ; Rao , P. S. GaCl3: A novel and an efficient reagent for the synthesis of homoallylic alcohols . Tetrahedron Lett. 2006 , 47 , 4315 – 4318 .
   Web of Science ®Google Scholar
• (a) Chen , J. ; Sakamoto , K. ; Orita , A. ; Otera , J. Bis (pentafluorophenyl) tin dibromide as a novel organotin halide Lewis acid catalyst . Synlett 1996 , 877 – 879 ; (b) Yanagisawa , A. ; Morodame , M. ; Nakashima , H. ; Yamamoto , H. Synthesis of 3-alkoxy indoles via palladium-catalyzed intramolecular cyclization of N-alkyl ortho-siloxyllyl anilines . Synlett 1997 , 1309 – 1311 ; (c) Kobayashi , S. Sc(OTf)3 in organic synthesis . Eur. J. Org. Chem. 1999 , 15 – 27 .
   Google Scholar
• (a) Kamble , R. M. ; Singh , V. K. An efficient method for allylation of ketones with tetra-allylstannane . Tetrahedron Lett. 2001 , 42 , 7525 – 7526 ; (b) Aspinall , H. C. ; Bissett , J. S. ; Greeves , N. ; Levin , D. La(OTf)3-catalysed allylation of aldehydes: Crucial activation by benzoic acid . Tetrahedron Lett. 2002 , 43 , 319 – 321 .
   Google Scholar
• (a) Narsaiah , A. V. LaCl3-accelerated conjugate addition of amines to electron-poor alkenes . Lett. Org. Chem. 2007 , 462 ; (b) Luche , J. L. ; Gemal , A. L. Efficient synthesis of acetals catalyzed by rare earth chlorides . Chem. Commun. 1978 , 976 – 877 ; (c) Narsaiah , A. V. ; Nagaiah , K. LaCl3-mediated regeneration of carbonyl compounds from oximes in water . Ind. J. Chem. 2003 , 2045 – 2047 ; (d) Narsaiah , A. V. ; Nagaiah , K. An efficient Knoevenagel condensation catalyzed by LaCl3 in heterogeneous medium . Synth. Commun. 2003 , 33 , 3825 – 3832 ; (e) Narsaiah , A. V. LaCl3: An efficient catalyst for the silylation of hydroxyl groups by activating HMDS . J. Organomet. Chem. 2007 , 692 , 3614 ; (f) Lu , J. ; Bai , Y. ; Wang , Z. ; Yang , B. ; Ma , H. One-pot synthesis of 3,4-DH-pyrimidin-2(1H)-ones using LaCl3 as a catalyst . Tetrahedron Lett. 2000 , 41 , 9075 – 9078 .
   Google Scholar