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Scientific article
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Diastereoselective and enantioselective reduction of tetralin- 1,4-dione

Published inBeilstein journal of organic chemistry, vol. 4, no. 37, p. 1-5
Publication date2008
Abstract

Background: The chemistry of tetralin-1,4-dione, the stable tautomer of 1,4-dihydroxynaphthalene, has not been explored previously. It is readily accessible and offers interesting opportunities for synthesis. Results: The title reactions were explored. L-Selectride reduced the diketone to give preferentially the cis-diol (d.r. 84 : 16). Red-Al gave preferentially the trans-diol (d.r. 13 : 87). NaBH4, LiAlH4, and BH3 gave lower diastereoselectivities (yields: 76–98%). Fractional crystallization allowed isolation of the cis-diol and the trans-diol (55% and 66% yield, respectively). Borane was used to cleanly give the mono-reduction product. Highly enantioselective CBS reductions afforded the trans-diol (72% yield, 99% ee) and the mono-reduction product (81%, 95% ee). Conclusion: Diastereoselective and enantioselective reductions of the unexplored tetralin-1,4-dione provides a very convenient entry into a number of synthetically highly attractive 1,4-tetralindiols and 4-hydroxy-1-tetralone.

Citation (ISO format)
KUNDIG, Ernst Peter, ENRIQUEZ-GARCIA, Alvaro. Diastereoselective and enantioselective reduction of tetralin- 1,4-dione. In: Beilstein journal of organic chemistry, 2008, vol. 4, n° 37, p. 1–5. doi: 10.3762/bjoc.4.37
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ISSN of the journal1860-5397
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