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Synthesis 2002(7): 0928-0936
DOI: 10.1055/s-2002-28504
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart · New York

NbCl5: A Novel Lewis Acid in Allylation Reactions

Carlos Kleber Z. Andrade*, Neucírio R. Azevedo, Guilherme R. Oliveira
Instituto de Química, Universidade de Brasília, C.P. 4478, 70910-970, Brasília, DF, Brazil
Fax: +55(61)2734149; e-Mail: ckleber@unb.br;
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Publication History

Received 3 March 2002
Publication Date:
14 May 2002 (online)

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Abstract

Allylation reactions promoted by niobium pentachloride are described. Allylstannanes were added to aromatic and aliphatic aldehydes and aromatic imines in good yields. Excellent syn dia­stereoselectivities were obtained in the addition of (E)-cinnamylstannane to benzaldehyde (49:1) and in the addition of crotylstannane to N-benzylideneaniline (46:1).

Key words

allylation - homoallylic compounds - stereoselectivity - niobium pentachloride - Lewis acids

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17

1H NMR (CDCl3) syn: δ = 1.94 (br, 1 H), 3.63 (t, 1 H, J = 8.0 Hz), 4.78-5.04 (m, 3 H), 5.89 (ddd, 1 H, J = 7.8, 10.3, 18.1 Hz), 7.01-7.38 (m, 10 H). For comparison, see ref. [27]

21

The choice for CH2Cl2 was based on the fact that the reaction in this solvent could be run at lower temperature (-78 °C) as compared to CH3CN.

26

For a complete discussion of the possible transition states geometries, see ref. [24]