Publikation: α-Thioalkylation of Zinc Dienolates as an Entry to 4-Substituted 1-tert-Butoxy-7a-methylhexahydroindenes
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French-Ukrainian Journal of Chemistry. 2015, 3(1), pp. 29-45. eISSN 2312-3222
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Hexahydroindenes 10 are readily available in 3 steps with an overall yield of 41 – 45 % starting from the Hajos Wiechert ketone 1. Alkylation of the α,β-unsaturated ketone 1 at C-4 has been achieved by thioalkylation of the corresponding zinc dienolate 2 with α-chlorosulfides of type 3. Subsequent in situ reduction and desulfurization of the β-(phenylthio) ketones 4 leads directly to the 4-substituted hexahydroindene-5-ols 6 which can be deoxygenated via their mesylates to the hexahydroindenes 10.
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KÖHLER, Thomas, Thomas HUHN, Ulrich GROTH, 2015. α-Thioalkylation of Zinc Dienolates as an Entry to 4-Substituted 1-tert-Butoxy-7a-methylhexahydroindenes. In: French-Ukrainian Journal of Chemistry. 2015, 3(1), pp. 29-45. eISSN 2312-3222BibTex
@article{Kohler2015Thioa-32233,
year={2015},
title={α-Thioalkylation of Zinc Dienolates as an Entry to 4-Substituted 1-tert-Butoxy-7a-methylhexahydroindenes},
url={http://kyivtoulouse.univ.kiev.ua/journal/index.php/fruajc/article/view/8},
number={1},
volume={3},
journal={French-Ukrainian Journal of Chemistry},
pages={29--45},
author={Köhler, Thomas and Huhn, Thomas and Groth, Ulrich}
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<dcterms:abstract xml:lang="eng">Hexahydroindenes 10 are readily available in 3 steps with an overall yield of 41 – 45 % starting from the Hajos Wiechert ketone 1. Alkylation of the α,β-unsaturated ketone 1 at C-4 has been achieved by thioalkylation of the corresponding zinc dienolate 2 with α-chlorosulfides of type 3. Subsequent in situ reduction and desulfurization of the β-(phenylthio) ketones 4 leads directly to the 4-substituted hexahydroindene-5-ols 6 which can be deoxygenated via their mesylates to the hexahydroindenes 10.</dcterms:abstract>
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2015-11-24
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