1052103-49-7Relevant articles and documents
Synthesis and Structural Elucidation of 1,2-Disubstituted 3-Fluoropiperidines
Evans, Paul,Fischer, Pauline,Müller-Bunz, Helge,Morris, Morgan
, (2020)
The work described details the reaction between Selectfluor and a series of 1-carbonyloxy and 1-sulfonyl 2-piperidines in order to generate 3-fluoro-2-methoxypiperidines 3a–f. Their subsequent reaction with allyltrimethylsilane, in the presence of BF3 and TiCl4, is then reported. Studies involving a combination of single-crystal X-ray crystallography and NMR spectroscopy indicate that the allylation process is cis-selective for both carbamate and sulfonamide variants and that optimal levels of diastereoselectivity are obtained using the N-2-nitrobenzene sulfonyl (2-Ns) group. In this manner, the synthesis of a series of 2-allyl 3-fluoro-substituted piperidines (5a, c–f) was achieved. The conversion of both the cis and trans-N-tosyl adducts (5d) into 3-fluorinated analogues of the natural products pelletierine (10) and coniine (11) is subsequently detailed.
Ring expansion of lactones and lactams via propiolate 1-carbon intercalation
Grant, Tina N.,Benson, Chantel L.,West
supporting information; experimental part, p. 3985 - 3988 (2009/05/30)
(Chemical Equation Presented) Readily available five- and six-membered lactones and N-sulfonyllactams undergo efficient addition of t-butyl propiolate, and the resulting adducts undergo cycloisomerization to six- and seven-membered cyclic ethers or amines in the presence of pyridinium acetate. The ring expansion process occurs in generally good yields and is proposed to involve a nucleophilic catalysis mechanism.
