"Super Silyl" Group for Diastereoselective Sequential Reactions: Access to Complex Chiral Architecture in One Pot
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- 作者：Matthew B. Boxer ; Hisashi Yamamoto
- 刊名：Journal of the American Chemical Society
- 出版年：2007
- 出版时间：March 14, 2007
- 年：2007
- 卷：129
- 期：10
- 页码：2762 - 2763
- 全文大小：389K
- 年卷期：v.129,no.10(March 14, 2007)
- ISSN：1520-5126
文摘
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.