'Super Silyl' Group for Diastereoselective Sequential Reactions: Access to Complex Chiral Architecture in One Pot
- UC
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 HNTf{sub 2}) 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.
- Research Organization:
- Advanced Photon Source (APS), Argonne National Laboratory (ANL), Argonne, IL (US)
- Sponsoring Organization:
- USDOE
- OSTI ID:
- 1007620
- Journal Information:
- J. Am. Chem. Soc., Journal Name: J. Am. Chem. Soc. Journal Issue: (10) ; 03, 2007 Vol. 129; ISSN JACSAT; ISSN 0002-7863
- Country of Publication:
- United States
- Language:
- ENGLISH
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