Nitroalkene Inter [4+ 2]/Intra [3+ 2] Tandem Cycloadditions. 7. Application of (R)-(-)-2, 2-Diphenylcyclopentanol as the Chiral Auxiliary

…, ME Schnute, LR Marcin, A Thorarensen

Index: Denmark, Scott E.; Schnute, Mark E.; Marcin, Lawrence R.; Thorarensen, Atli Journal of Organic Chemistry, 1995 , vol. 60, # 10 p. 3205 - 3220

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Citation Number: 57

Abstract

Chiral enol ethers derived from (R)-(-)-2, 2-diphenylcyclopentanol ((-)-3) have been found to provide high levels of asymmetric induction in tandem inter [4+ 2Yintra [3+ 21 nitroalkene cycloadditions. The chiral auxiliary ('97% ee) is readily prepared in three steps from diphenylacetonitrile employing an asymmetric oxazaborolidine-catalyzed borane reduction. Either enantiomeric series of tandem cycloadditionhydrogenolysis product 7 is available ...