Organic letters

α-Hydroxy Cyclopentenones from α-Diketones

WA Batson, D Sethumadhavan, MA Tius

Index: Batson, William A.; Sethumadhavan, Divakaramenon; Tius, Marcus A. Organic Letters, 2005 , vol. 7, # 13 p. 2771 - 2774

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Citation Number: 18

Abstract

The Yb(OTf) 3 -catalyzed reactions were performed in DMSO in the presence of pyrrolidine. 11 Although we were tempted to postulate an enamine intermediate, this is unlikely to be the case, since the cyclization also took place when N-methylpyrrolidine was used in place of pyrrolidine. The Lewis acid catalyzed process appears to take place under kinetic control. For example, diketone 7 (Table 1, entry 1) leads to a ca. 4/1 mixture of products 8 and 9. The ...