Journal
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Volume 4, Issue -, Pages -Publisher
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.4.37
Keywords
asymmetric; catalysis; ketone; reduction; tautomer
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Funding
- Swiss National Science Foundation [200020_119947/1]
- Swiss National Science Foundation (SNF) [200020_119947] Funding Source: Swiss National Science Foundation (SNF)
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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.
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