105885-67-4Relevant academic research and scientific papers
Efficient synthesis of chlorohydrins using ClCH2MgCl·LiCl
Nishimura, Rodolfo H.V.,Toledo, Fabiano T.,Lopes, Jo?o L.C.,Clososki, Giuliano C.
, p. 287 - 290 (2013)
The mixed lithium-magnesium carbenoid ClCH2MgCl·LiCl was easily generated in THF through the reaction of chloroiodomethane with i-PrMgCl·LiCl at -78 °C. This reagent reacts well with a number of aldehydes to give the corresponding chlorohydrins in good yields.
Synthesis of enantiopure chloroalcohols by enzymatic kinetic resolution
Haak, Robert M.,Tarabiono, Chiara,Janssen, Dick B.,Minnaard, Adriaan J.,De Vries, Johannes G.,Feringa, Ben L.
, p. 318 - 323 (2007)
3-Alkenyl and heteroaryl chloroalcohols have been obtained in excellent enantiomeric excess (>99%) by enzymatic kinetic resolution using the haloalcohol dehalogenase HheC. Yields were close to the theoretical maximum for all substrates employed. Furthermo
(CHLOROMETHYL)LITHIUM IN AN EFFICIENT CONVERSION OF CARBONYL COMPOUNDS TO CHLOROHYDRINS OR OXIRANES
Sadhu, Kizhakethil Mathew,Matteson, Donald S.
, p. 795 - 798 (1986)
(Chloromethyl)lithium has been generated and captured in nearly quantitative yields by addition of n-butyllithium or methyllithium to mixtures of chloroiodomethane with aldehydes or ketones in THF at -78 grad C.Immediate acidification yields chlorohydrins, delayed workup yields epoxides.
Mild stereoselective formation of tri- and tetrasubstituted olefins by regioselective ring opening of 1,1-disubstituted vinyl oxiranes with dialkyl dithiophosphates
Guo, Boying,Vitaku, Edon,Njardarson, Jon T.
supporting information, p. 3232 - 3234 (2014/06/09)
Presented in this Letter is a mild new method to stereoselectively ring open 1,1-disubstituted vinyl oxiranes using dialkyl dithiophosphate nucleophiles. This new reaction proceeds in toluene at room temperature to afford tri- and tetrasubstituted allylic alcohols with high Z-selectivity. The syn relationship between the alcohol and the newly incorporated dithiophosphate moiety presented an opportunity to evaluate the anionic hopping properties of the ring opening product. Treatment of the ring opening product with base results in a facile phosphate hopping followed by a selective thiolate 3-exo-trig instead of a 5-exo-tet cyclization.
Chemoselective cross metathesis of bishomoallylic alcohols: Rapid access to fragment A of the cryptophycins
Lautens, Mark,Maddess, Matthew L.
, p. 1883 - 1886 (2007/10/03)
Equation presented. The racemic or enantioselective allylation of in situ formed β,γ-unsaturated aldehydes provides efficient access to bishomoallylic alcohols from readily available 2-vinyloxiranes. These products, when subjected to modified Grubbs cross
Enantioselective allylation of β,γ-unsaturated aldehydes generated via Lewis acid induced rearrangement of 2-vinyloxiranes
Lautens, Mark,Maddess, Matthew L.,Sauer, Effiette L. O.,Ouellet, Stephane G.
, p. 83 - 86 (2007/10/03)
(matrix presented) 2-Vinyloxiranes have been found to be excellent surrogates to β,γ-unsaturated aldehydes. These valuable electrophiles, generated in situ by treatment of a 2-vinyloxirane with a catalytic amount of Sc(OTf)3, are effectively tr
