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Synthesis 2006(7): 1103-1110
DOI: 10.1055/s-2006-926381
DOI: 10.1055/s-2006-926381
PAPER
© Georg Thieme Verlag Stuttgart · New York
Synthesis of 3-Alkyl- and 3-Chloroalkyl-2-hydroxybenzoates Based on [3+3] Cyclizations of 4-Alkyl- and 4-Chloroalkyl-1,3-bis(trimethylsilyloxy)buta-1,3-dienes
Further Information
Received
29 August 2005
Publication Date:
08 March 2006 (online)
Publication History
Publication Date:
08 March 2006 (online)
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Abstract
The TiCl4-mediated [3+3] cyclization of 4-alkyl- and 4-chloroalkyl-1,3-bis(trimethylsilyloxy)buta-1,3-dienes with 3-silylalk-2-en-1-ones afforded 3-alkyl- and 3-chloroalkyl-2-hydroxybenzoates, respectively; the latter containing a remote chloride functionality. The TiCl4- and TiBr4-mediated [3+3] cyclization of 1,3-bis(trimethylsilyloxy)-4-chloroalkylbuta-1,3-dienes with 1,1-diacetylcyclopropane afforded salicylates containing two remote halide functionalities.
Key words
arenes - cyclizations - domino reactions - silyl enol ethers
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References
Nguyen, V. T. H.; Bellur, E.; Appel, B.; Langer, P., unpublished results.