3899-89-6Relevant academic research and scientific papers
A direct C-C cross-coupling of alcohols at the β-position with aldehydes under co-promotion of tris(triphenylphosphine)-rhodium chloride/boron trifuoride etherate
Zhang, Shu-Yu,Tu, Yong-Qiang,Fan, Chun-An,Jiang, Yi-Jun,Shi, Lei,Cao, Ke
supporting information; experimental part, p. 2189 - 2193 (2009/10/02)
The novel tris(triphenylphosphine)rhodium chloride/boron trifuoride etherate [RhCl-(PPh3)3/BF3·OEt 2] co-promoted the C-C cross-coupling of tertiary alcohols at the β-position with aldehydes. This reaction provides an efficient synthesis of either structurally diverse 1,3-diols or polysubstituted tetrahydropyrans by controlling the substrate structures, and it could be developed to a practical syntheticmet hod for numerous natural products and medicinally important compounds.
1,3-Diol synthesis via controlled, radical-mediated C-H functionalization
Chen, Ke,Richter, Jeremy M.,Baran, Phil S.
, p. 7247 - 7249 (2008/12/21)
The invention of a method for the synthesis of 1,3-diols from the corresponding alcohols is described, via controlled, radical-mediated C-H functionalization. The sequence described herein entails near quantitative conversion to the corresponding trifluoroethyl carbamate, followed by a variant of the Hofmann-Loffler-Freytag reaction, cyclization, and hydrolysis to provide the 1,3-diols. In addition to the 10 examples presented herein, the syntheses of four natural products are facilitated by this directed oxyfunctionalization. This methodology is demonstrated to be orthogonal to other known C-H oxidations. Finally, this sequence is efficient, practical, inexpensive, and scalable. Copyright
