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Synthesis 1972; 1972(10): 526-532
DOI: 10.1055/s-1972-21911
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Reductions of Functional Groups with Sulfurated Borohydrides. Application to Steroidal Ketones

J. M. LALANCETTE* , A. FRÊCHE, J. R. BRINDLE, M. LALIBERTÉ
  • *Département de Chimie, Faculté des Sciences, Université de Sherbrooke, Sherbrooke, Qué, Canada
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Publication History

Publication Date:
12 September 2002 (online)

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Sulfurated borohydrides can be prepared very easily from the corresponding borohydrides. These sulfurated borohydrides show selective properties as reducing and sulfurating agents that offer real synthetic interest. A review of the reactions of the main functional groups with NaBH2S3 is presented, along with the reductions observed with steroidal ketones. 1. Preparation of Borohydrides incorporating Sulfur, Selenium, or Tellurium 1.1. Sulfurated Sodium Borohydride 1.2. Borohydrides incorporating Selenium and Tellurium 2. Reactions with Sulfurated Borohydrides 2.1. Reduction of Aldehydes 2.2. Reduction of Ketones 2.3. Reduction of Functional Groups incorporating Nitrogen 2.4. Preparation of Thioacetals 2.5. Reactions of NaBH2S3 with Epoxides 2.6. Reduction of Carboxylic Acid Derivatives 2.7. Selective Reduction of Aldehydes and Ketones 2.8. Reduction of Steroidal Ketones

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