One-Pot in Situ Formation and Reaction of Trimethyl(trichloromethyl)silane: Application to the Synthesis of 2,2,2-Trichloromethylcarbinols
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- 作者：Kevin E. Henegar ; Ricardo Lira
- 刊名：The Journal of Organic Chemistry
- 出版年：2012
- 出版时间：March 16, 2012
- 年：2012
- 卷：77
- 期：6
- 页码：2999-3004
- 全文大小：259K
- 年卷期：v.77,no.6(March 16, 2012)
- ISSN：1520-6904
文摘
2,2,2-Trichloromethylcarbinols are 1 are valuable synthetic intermediates with a multitude of uses. A scalable procedure for the synthesis of TMS-protected-2,2,2-trichloromethylcarbinols and 2,2,2-trichloromethylcarbinols 1 was developed that employs the in situ generation and reaction of trimethyl(trichloromethyl)silane (CCl3-TMS). The procedure avoids the exposure of the carbonyl compounds to the strongly basic conditions typically used for this transformation and also avoids isolation of the difficult-to-handle CCl3-TMS. This procedure was applied to diastereoselective trichloromethyl additions to 2-substituted 4-piperidinones and to reactions with a variety of structurally diverse aldehydes and ketones.