20739-58-6Relevant articles and documents
-
Sood,R. et al.
, p. 423 - 425 (1974)
-
Transmetallation from aluminum to tin: A facile preparation of tributylstannylprop-2-en-1-ols
Havranek, Miroslav,Dvorak, Dalimil
, p. 1264 - 1268 (1998)
3-Substituted 3-tributylstannylprop-2-en-1-ols 2 can be efficiently prepared by hydroalumination of 3-substituted propargyl alcohols 1 with LiAlH4 and subsequent transmetallation to tin employing Bu3SnOMe instead of the commonly used Bu3SnOTf or Bu3SnCl.
Chemoselective Oxidation of p-Methoxybenzyl Ethers by an Electronically Tuned Nitroxyl Radical Catalyst
Hamada, Shohei,Sugimoto, Koichi,Elboray, Elghareeb E.,Kawabata, Takeo,Furuta, Takumi
supporting information, p. 5486 - 5490 (2020/07/24)
The oxidation of p-methoxy benzyl (PMB) ethers was achieved using nitroxyl radical catalyst 1, which contains electron-withdrawing ester groups adjacent to the nitroxyl group. The oxidative deprotection of the PMB moieties on the hydroxy groups was observed upon treatment of 1 with 1 equiv of the co-oxidant phenyl iodonium bis(trifluoroacetate) (PIFA). The corresponding carbonyl compounds were obtained by treating the PMB-protected alcohols with 1 and an excess of PIFA.
Synthesis of solandelactone F, constanolactone A and an advanced intermediate towards solandelactone e from a common synthetic intermediate
Yalla, Raju,Raghavan, Sadagopan
, p. 4572 - 4592 (2019/05/16)
The stereoselective synthesis of solandelactone F, constanolactone A and an advanced intermediate towards solandelactone E, from a common synthetic intermediate, is disclosed. The propargylic sulfide stereocenter is created stereoselectively via carbon-carbon bond formation in the reaction of α-chloro sulfides with alkynylzinc reagents via 1,2-asymmetric induction by a β-siloxy group. The characteristic 1,4-diol motif of the natural products is introduced by a [2,3] sigmatropic rearrangement of an allylic sulfoxide or by the Mislow-Evans-Braverman rearrangement of a propargylic sulfoxide followed by stereoselective reduction of the ensuing α,β-unsaturated ketone. Unlike earlier reports, the C11/C9 carbinol center is created with excellent stereocontrol and derivatives of natural products differing at C14/C12 can be readily obtained. Catalytic asymmetric protocols and substrate-controlled asymmetric induction are utilized for the efficient introduction of the stereogenic centers.
