25695-95-8Relevant articles and documents
Modular Construction of Protected 1,2/1,3-Diols, -Amino Alcohols, and -Diamines via Catalytic Asymmetric Dehydrative Allylation: An Application to Synthesis of Sphingosine
Tanaka, Shinji,Gunasekar, Ramachandran,Tanaka, Tatsuya,Iyoda, Yoko,Suzuki, Yusuke,Kitamura, Masato
, p. 9160 - 9170 (2017/09/11)
A new enantioselective catalysis has been developed for the one-step construction of methylene-bridged chiral modules of 1,2- and 1,3-OH and/or NH function(s) from δ- or λ-OH/NHBoc-substituted allylic alcohols and H2C=O / H2C=NBoc . A protonic nucleophile, either in situ-generated CH2OH or CH2NHBoc, is intramolecularly allylated to furnish eight possible 1,2- or 1,3-O,O, -O,N, -N,O, and -N,N chiral modules equipped with an ethenyl group in high yields and enantioselectivities. The utility of this method has been demonstrated in the five-step synthesis of sphingosine.
Chemo-, regio-, and stereoselective silver-catalyzed aziridination of dienes: Scope, mechanistic studies, and ring-opening reactions
Llaveria, Josep,Beltrán, álvaro,Sameera,Locati, Abel,Díaz-Requejo, M. Mar,Matheu, M. Isabel,Castillón, Sergio,Maseras, Feliu,Pérez, Pedro J.
, p. 5342 - 5350 (2014/05/06)
Silver complexes bearing trispyrazolylborate ligands (Tpx) catalyze the aziridination of 2,4-diene-1-ols in a chemo-, regio-, and stereoselective manner to give vinylaziridines in high yields by means of the metal-mediated transfer of NTs (Ts = p-toluensulfonyl) units from PhI=NTs. The preferential aziridination occurs at the double bond neighboring to the hydroxyl end in ca. 9:1 ratios that assessed a very high degree of regioselectivity. The reaction with the silver-based catalysts proceeds in a stereospecific manner, i.e., the initial configuration of the C=C bond is maintained in the aziridine product (cis or trans). The degree of regioselectivity was explained with the aid of DFT studies, where the directing effect of the OH group of 2,4-diene-1-ols plays a key role. Effective strategies for ring-opening of the new aziridines, deprotection of the Ts group, and subsequent formation of β-amino alcohols have also been developed.
Synthesis of D/L-erythro-Sphingosine Using a Tethered Aminohydroxylation Reaction as the Key Step
Morales-Serna, Jose Antonio,Isabel Matheu, Yolanda Diaz M.,Castillon, Sergio
experimental part, p. 710 - 712 (2009/09/06)
A diastereoselective synthesis of racemic D/L-erythro- sphingosine is described. The approach involves employing tethered aminohydroxylation (TA) to introduce the 2-amino and 3- hydroxy functions with required stereochemistry. Georg Thieme Verlag Stuttgart.
