An internally activated tin hydride with enhanced reducing ability

E Vedejs, SM Duncan, AR Haight

Index: Vedejs, E.; Duncan, S. M.; Haight, A. R. Journal of Organic Chemistry, 1993 , vol. 58, # 11 p. 3046 - 3050

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Citation Number: 85

Abstract

Tin hydride 1 is activated for nucleophilic hydride transfer and also for radical chain reduction, depending on solvent. The nucleophilic hydride pathway is favored in methanol, and 1 can be used as a selective reducing agent for ketones. Simple ketones are not reduced in aprotic solvents, but 8-hydroxy ketones are activated internally by the hydroxyl group and can be reduced in THF with good control of stereochemistry, as in the ...

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