Enantioselective intramolecular cyclopropanations of allylic and homoallylic diazoacetates and diazoacetamides using chiral dirhodium (II) carboxamide catalysts

…, MP Dwyer, AB Dyatkin, AV Kalinin…

Index: Doyle, Michael P.; Austin, Richard E.; Bailey, A. Scott; Dwyer, Michael P.; Dyatkin, Alexey B.; Kalinin, Alexey V.; Kwan, Michelle M. Y.; Liras, Spiros; Oalmann, Christopher J.; Pieters, Roland J.; Protopopova, Marina N.; Raab, Conrad E.; Roos, Gregory H. P.; Zhou, Qi-Lin; Martin, Stephen F. Journal of the American Chemical Society, 1995 , vol. 117, # 21 p. 5763 - 5775

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Citation Number: 225

Abstract

Abstract: Diazo decomposition of allylic and homoallylic diazoacetates loa-p and 22a-j catalyzed by chiral dirhodium (I1) tetrakis [methyl 2-pyrrolidone-S (S)-carboxylate], Rhz (SS- MEPY) 4 (7), and its enantiomer, Rhz (5R-MEPY) 4 (S), produces the corresponding intramolecular cyclopropanation products lla-p and 23a-j in good to excellent yields and with exceptional enantioselectivity. Higher enantiocontrol is observed with allylic diazoacetates ...