181303-63-9Relevant academic research and scientific papers
Efficient and mild method for preparation of allylic amines from aziridine-2-alcohols using PPh3/I2/imidazole
Chavan, Subhash P.,Khairnar, Lalit B.,Chavan, Prakash N.
, p. 5905 - 5907 (2014)
Allylic amines are synthesized in good to excellent yields by treatment of aziridine-2-alcohols with PPh3/I2/imidazole in THF as solvent under mild conditions.
Application of allylic amine formation from aziridine-2-ol under Appel reaction condition: Synthesis of N-(tert-butoxycarbonyl)-D-vinyl glycine methyl ester
Chavan, Subhash P.,Kawale, Sanket A.,Patil, Niteen B.,Kalbhor, Dinesh B.
, (2021/05/18)
PPh3/I2/imidazolde mediated allyl amine formation from aziridine-2-alcohol was explored for the synthesis of N-(tert-butoxycarbonyl)-D-vinyl glycine methyl ester.
Study of the reactions between vinylmagnesium bromide and imines derived from (R)-glyceraldehyde - The key step in the stereodivergent synthesis of conveniently protected, enantiopure syn- and anti-2-amino-1,3,4-butanetriol derivatives
Badorrey, Ramon,Cativiela, Carlos,Diaz-de-Villegas, Maria D.,Diez, Roberto,Galvez, Jose A.
, p. 2268 - 2275 (2007/10/03)
A total stereodivergent method for the synthesis of enantiopure syn- and anti-2-amino-1,3,4-butanetriol (ABT) derivatives from inexpensive and readily available D-mannitol has been developed. Key steps include: (a) the diastereoselective addition of vinylmagnesium bromide to conveniently protected N-benzylimines derived from (R)-glyceraldehyde, and (b) the oxidative degradation of the C-C double bond of the resultant syn- and anti-vinylaminodiol derivatives. The addition of vinylmagnesium bromide in diethyl ether to the N-benzylimine derived from (R)-2,3-O-isopropylideneglyceraldehyde affords the anti-vinylaminodiol derivative, while the reaction with the N-benzylimine derived from (R)-2,3-di-Obenzylglyceraldehyde affords the syn-vinylaminodiol derivative, both with excellent diastereoselectivities (de > 98/2). Moreover, a reversal of the stereochemical course of the reaction is produced when (R)-2,3-O-isopropylideneglyceraldehyde N-benzylimine is precomplexed with ZnI2, in this case yielding the syn addition adduct as the major compound. Different reaction conditions (reagent molar ratio, reaction temperature) have been tested in order to determine their influences on the observed yields and diastereo-selectivities. From the results of this study and a subsequent crossover experiment, some interesting mechanistic considerations can be inferred. Enantiopure anti- and syn-vinylaminodiol adducts have been successfully converted into conveniently protected anti- and syn-2-amino-1,3,4-butanetriol (ABT) derivatives, key building blocks in the asymmetric synthesis of biologically active compounds. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
A general method for the vinylation of nitrones. Synthesis of allyl hydroxylamines and allyl amines
Merino, Pedro,Anoro, Sonia,Franco, Santiago,Gascon, Jose M.,Martin, Victor,Merchan, Francisco L.,Revuelta, Julia,Tejero, Tomas,Tunon, Victoria
, p. 2989 - 3021 (2007/10/03)
An examination of the vinylation of several nitrones is presented. Whereas a complete diastereofacial discrimination was observed upon the addition of vinyl organometallic reagents to α-alkoxy nitrones, the same reaction with α-amino nitrones gave syn add
Direct vinylation and ethynylation of nitrones. Stereodivergent synthesis of allyl and propargyl amines
Merino, Pedro,Anoro, Sonia,Castillo, Elena,Merchan, Francisco,Tejero, Tomas
, p. 1887 - 1890 (2007/10/03)
The addition of vinyl and ethynyl organometallic reagents to the nitrone derived from D-glyceraldehyde affords allyl and propargyl hydroxylamines which are easily converted into the corresponding allyl and propargyl amines. The stereoselectivity of the addition step can be controlled by the presence (or absence) of diethyl aluminium chloride.
