138567-55-2Relevant academic research and scientific papers
Regioselective nucleophilic ring opening of epoxides and aziridines derived from homoallylic alcohols
Tanner, David,Groth, Thomas
, p. 16139 - 16146 (1997)
The regioselectivity of nuclcopbilic ring opening of some 3,4-epoxy and 3,4-aziridino alcohols has been studied. The nucleophiles chosen were complex hydrides (LiAlH4, Red-Al and DIBAL) and Lipshutz- or Gilman-type organocuprate reagents. The C-4 substituent in the substrates was varied in order to study steric and electronic effects on the ring opening reactions. For alkyl substituents at C-4, most of the results can be explained on the basis of intramolecular delivery of the nucleophile to C-3 via a six-membered transition state, leading to 1,4-diols or 1,4-amine alcohol derivatives. In general, the epoxy alcohols gave poorer regioselectivity than the N-tosyl aziridino alcohols, for which selectivities of >95:5 were routinely obtained. The activating effect of a phenyl group at C-4 led to a switch in regiochemistry, with the 1,3-diol or 1,3-amino alcohol derivative as the major product.
Copper-Catalyzed Diastereoselective Synthesis of Trifluoromethylated Tetrahydrofurans
Wang, Yanan,Jiang, Min,Liu, Jin-Tao
supporting information, p. 1322 - 1327 (2016/04/26)
The copper-catalyzed intramolecular diastereoselective trifluoromethylcycloetherification of homoallylic alcohols with Togni's reagent as trifluoromethylating reagent was realized under mild conditions. Various trifluoromethylated tetrahydrofurans were synthesized in moderate to good yields. Moreover, a wide range of common functional groups was tolerated.
Asymmetric 5-endo chloroetherification of homoallylic alcohols toward the synthesis of chiral β-chlorotetrahydrofurans
Zeng, Xianghua,Miao, Chengxia,Wang, Shoufeng,Xia, Chungu,Sun, Wei
supporting information, p. 2418 - 2420 (2013/04/10)
An asymmetric 5-endo chloroetherification of homoallylic alcohols is successfully developed that employs an easily available quaternary ammonium salt derived from cinchonine as a conventional organocatalyst. This approach provides ready access to β-chloro
The Copper(I)-catalysed Coupling of Grignard Reagents with 5-Lithio-2,3-dihydrofuran and 6-Lithio-3,4-dihydro-2H-pyran
Barber, Christopher,Bury, Paul,Kocienski, Philip,O'Shea, Michael
, p. 1595 - 1597 (2007/10/02)
The organocuprates derived from reaction of Grignard reagents with CuBr*Me2S react with 5-lithio-2,3-dihydrofuran and 6-lithio-3,4-dihydro-2H-pyran via a 1,2-metallate rearrangement to generate an alkenylmagnesium cuprate.
