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Asymmetric Catalysis of Intramolecular Cyclopropanation of 5‐Aryl‐1‐diazo‐1‐mesitylsulfonyl‐5‐hexen‐2‐ones
Author(s) -
Sawada Takashi,
Nakada Masahisa
Publication year - 2005
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200505173
Subject(s) - substituent , cyclopropanation , chemistry , diazo , intramolecular force , aryl , methylenedioxy , medicinal chemistry , stereochemistry , catalysis , organic chemistry , alkoxy group , alkyl
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).