The scope of catalytic enantioselective tandem carbonyl ylide formation-intramolecular [3+ 2] cycloadditions

DM Hodgson, AH Labande, FYTM Pierard…

Index: Hodgson, David M.; Labande, Agnes H.; Pierard, Francoise Y. T. M.; Exposito Castro, Maria A. Journal of Organic Chemistry, 2003 , vol. 68, # 16 p. 6153 - 6159

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Citation Number: 83

Abstract

Catalytic enantioselective tandem carbonyl ylide formation-intramolecular 1, 3-dipolar cycloaddition reactions of 2-diazo-3, 6-diketoesters show promising scope in terms of asymmetric induction as the tethered alkene/alkyne dipolarophile component is varied. Cycloadditions were found to occur in moderate to very good yields, with a difference in ee exhibited by the electronically different 2-diazo-3, 6-diketoesters 1, 25 and 33, 34. Values ...