The Journal of organic chemistry

High selectivity from configurational match/mismatch in carbon-hydrogen insertion reactions of steroidal diazoacetates catalyzed by chiral dirhodium (II) …

MP Doyle, SB Davies, EJ May

Index: Doyle, Michael P.; Davies, Simon B.; May, Eric J. Journal of Organic Chemistry, 2001 , vol. 66, # 24 p. 8112 - 8119

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Citation Number: 40

Abstract

Diazo decomposition of steroidal diazoacetates, where the point of attachment is the 3- position of the steroid A-ring, catalyzed by chiral dirhodium (II) carboxamidates results in products from carbon-hydrogen insertion in high yield and selectivities. Use of S-configured catalysts shows a distinctive preference for insertion into the 3-position to form β-lactone products. The R-configured catalysts direct insertion preferentially to the equatorial CH ...