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Intramolecular Diels-Alder reactions involving boryl-3-propenoic acid derivatives

✍ Scribed by Guillaume Lorvelec; Michel Vaultier

Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
228 KB
Volume
39
Category
Article
ISSN
0040-4039

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✦ Synopsis

The coupling of 1,3-dienyl alcohols with boryl-3-propenoic acid 1 or of 1,3-dienyl secondary amines with the acid chloride 2 leads to the trienes 5 and 6 respectively. These are well suited precursors for an intramolecular Diels-Alder reaction leading to bicyclic cycloadducts having a carbonboron bond which can be stereoselectively transformed into a C-O or C-C bond. Thus, the cycloadduct 9 gave the interesting compound 10 via a simple oxidation-reduction sequence or the new boronate 11 via a Matteson's homologation. The introduction of chirality at nitrogen or boron in the trienyl amide 6b did not lead to interesting levels of asymmetric induction.

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