Department of Biochemistry and Chemistry , University of California , Los Angeles , California 90095 , United States.
J Org Chem. 2019 Mar 15;84(6):3652-3655. doi: 10.1021/acs.joc.8b03223. Epub 2019 Mar 6.
Silyl triflate precursors to cyclic alkynes and allenes serve as valuable synthetic building blocks. We report a concise and scalable synthetic approach to prepare the silyl triflate precursors to cyclohexyne and 1,2-cyclohexadiene. The strategy involves a retro-Brook rearrangement of an easily accessible cyclohexanone derivative, followed by triflation protocols. This simple, yet controlled, method should enable the further study of strained alkynes and allenes in chemical synthesis.
硅基三氟甲磺酸酯前体是环状炔烃和丙二烯的重要合成砌块。我们报道了一种简洁且可规模化的方法，用于合成环己炔和 1,2-环己二烯的硅基三氟甲磺酸酯前体。该策略涉及一种易获得的环己酮衍生物的反-Brook 重排，然后进行三氟甲磺酸酯化反应。这种简单而可控的方法应该能够促进在化学合成中对张力炔烃和丙二烯的进一步研究。
