Novel syn intramolecular pathway in base-catalyzed 1, 2-elimination reactions of β-acetoxy esters

…, HK Carlson, JM Coughlin, GE Hofmeister…

文献索引：Mohrig, Jerry R.; Carlson, Hans K.; Coughlin, Jane M.; Hofmeister, Gretchen E.; McMartin, Lea A.; Rowley, Elizabeth G.; Trimmer, Elizabeth E.; Wild, Andrew J.; Schultz, Steve C. Journal of Organic Chemistry, 2007 , vol. 72, # 3 p. 793 - 798

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被引用次数: 11

摘要

As part of a comprehensive investigation of electronic effects on the stereochemistry of base- catalyzed 1, 2-elimination reactions, we observed a new syn intramolecular pathway in the elimination of acetic acid from β-acetoxy esters and thioesters. 1H and 2H NMR investigation of reactions using stereospecifically labeled tert-butyl (2 R*, 3 R*)-3-acetoxy-2, 3-2H2-butanoate (1) and its (2 R*, 3 S*) diastereomer (2) shows that 23±2% syn ...