Kündig EP Enriquez-Garcia A 2008 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). NaBH(4), LiAlH(4), and BH(3) 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. application/pdf https://sonar.rero.ch/global/documents/169505 eng info:eu-repo/semantics/altIdentifier/doi/10.3762/bjoc.4.37 info:eu-repo/semantics/altIdentifier/pmid/19043623 info:eu-repo/semantics/openAccess Beilstein journal of organic chemistry. - 2008 asymmetric catalysis ketone reduction tautomer Diastereoselective and enantioselective reduction of tetralin-1,4-dione. http://purl.org/coar/resource_type/c_6501