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

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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7

Nguyen, V. T. H.; Bellur, E.; Appel, B.; Langer, P., unpublished results.