Diastereoselective reduction of cyclohexanones with diisobutylaluminium phenoxides in terms of the isoinversion principle

MA Meyer-Stork

Index: Meyer-Stork, Markus A.; Haag, Dieter; Scharf, Hans-Dieter Journal of the Chemical Society. Perkin Transactions 2, 1997 , # 3 p. 593 - 595

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Citation Number: 2

Abstract

The diastereoselectivity of the reduction of 2-substituted cyclohexanones 1–6 with 4- substituted diisobutylaluminium phenoxides a–d has been investigated as a function of temperature. The high-temperature region is found to be dominated by hydride transfer, which is controlled by steric as well as electronic effects. However, at low temperatures the Meerwein–Ponndorf–Verley reaction gains in importance. This phenomenon is quantified ...