title: Diastereoselective and enantioselective reduction of tetralin-1,4-dione.
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). 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).
  
  
  CONCLUSIONS
  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.
authors.affiliation: Department of Organic Chemistry, University of Geneva, 1211 Geneva 4, Switzerland. peter.kundig@unige.ch
authors.forename: E Peter
authors.initials: EP
authors.lastname: Kündig
authors.forename: Alvaro
authors.initials: A
authors.lastname: Enriquez-Garcia