We have examined the catalytic asymmetric intramolecular cyclopropanation (IMCP) reactions of 5-aryl-1-diazo-1-mesitylsulfonyl-5-hexen-2-ones, and found that the substituent of the 5-aryl group dramatically changes the enantioselectivity. That is, no enantioselectivity was observed when the substituent was a methoxy group; however, enantioselectivity was moderate when the substituent was a methylenedioxy group or a tert-butyldimethylsilyloxy group, and it dramatically increased when the substituent was lacking (96% ee) or a benzoyloxy group (93% ee).
|Number of pages||6|
|Journal||Advanced Synthesis and Catalysis|
|Publication status||Published - 2005 Oct 1|
- Asymmetric catalysis
- Diazo compounds
ASJC Scopus subject areas
- Organic Chemistry