Tetrahedron letters

Improved formal preparation of enantiomerically pure anti-benzo [a] pyrene diol epoxide

GR Negrete, T Meehan

文献索引：Negrete, George R.; Meehan, Thomas Tetrahedron Letters, 1994 , vol. 35, # 27 p. 4727 - 4730

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被引用次数: 7

摘要

Abstract We report an improved, economical formal route to enantiomerically pure anti- benzo [a] pyrene diol epoxide (BPDE). A trimethylaluminum catalyzed regio-and stereoselective opening of racemic 7, 8-epoxy-7, 8, 9, 10-tetrahydrobenzo [a] pyrene with Mosher's acid delivers benzylic esters exclusively. This step is a significant improvement over the lack of regioselectivity of standard procedures. We also show that modification of ...