Polymer-supported silyl cyanide and silyl azide: Useful reagents for solid-phase applications

✍ Scribed by Andrea Missio; Carla Marchioro; Tino Rossi; Mauro Panunzio; Simona Selva; Pierfausto Seneci

• Publisher: John Wiley and Sons
• Year: 2000
• Tongue: English
• Weight: 121 KB
• Volume: 71
• Category: Article
• ISSN: 0006-3592
• DOI: 10.1002/(sici)1097-0290(200024)71:1<38::aid-bit6>3.0.co;2-b

✦ Synopsis

The support of a delicate reagent on a solid matrix allows for better and safer handling of the reagent itself. Because we had an interest in silicon-based supported reagents 1 we turned our attention to a polymer-supported trialkylsilyl cyanide and trialkylsilyl azide starting from a commercially available trialkylsilane resin. The supported cyanide was obtained with excellent yield and proved to be shelf-stable. This supported reagent was reacted with a series of aldehydes and ketones yielding the corresponding polymer-supported cyanohydrins in good-to-excellent yields. A stability study on a model cyanohydrin demonstrated that these supported intermediates also can be stored for a prolonged time. For the last step, a cleavage strategy that could release either cyanohydrins or ␣-hydroxy esters was adopted. Finally, we prepared a polymer-supported trialkylsilyl azide, which also proved to be shelf-stable.