Selective monodeprotection of bis-silyl ethers

The challenge of increasingly complex synthetic targets points to the continued use of protection/deprotection protocols in synthetic organic chemistry. Although the more traditional methods of deprotection of silyl ethers such as acid- and fluoride-mediated techniques are still widely used and often allow excellent chemoselectivity, the development of new methods fill specialized roles and may allow for selective desilylation without unwanted side reactions. The effect of changing the electronic environment on the silyl group can be profound in affecting the selectivity in deprotection reactions. But, with the exception of alkoxy-substituted silyl protecting groups, this remains an open area of research. Similarly, neighboring groups can mediate the delivery of reagents to specific silyl ethers and allow for selective deprotection. But, this has been largely unexploited with the exception of neighboring carbonyl groups directing the selective deprotection of aryl silyl ethers in the presence of other aryl silyl ethers.