875288-47-4Relevant articles and documents
"Super silyl" group for diastereoselective sequential reactions: Access to complex chiral architecture in one pot
Boxer, Matthew B.,Yamamoto, Hisashi
, p. 2762 - 2763 (2007/10/03)
We have shown that the tris(trimethylsilyl)silyl (TTMSS) silyl enol ether of acetaldehyde undergoes aldehyde cross-aldol reactions with high selectivity and the extremely low catalyst loading (0.05 mol % of HNTf2) allows for one-pot sequential reactions where acidic or basic nucleophiles can be subsequently added. Various ketone-derived silyl enol ethers, Grignard reagents, and dienes succeeded, generating relatively complex molecular architectures in a single step. This represents the first case where, in a single pot, highly acidic conditions followed by very basic conditions were tolerated to give products with high diastereoselectivities and good yields. Copyright