1338801-20-9Relevant academic research and scientific papers
A General Synthesis of Sphinganines through Multicomponent Catalytic Asymmetric Aziridination
Mukherjee, Munmun,Zhou, Yubai,Gupta, Anil K.,Guan, Yong,Wulff, William D.
supporting information, p. 1386 - 1390 (2015/10/05)
A catalytic asymmetric synthesis of all four stereoisomers of sphinganine is described starting from hexadecanal. Utilizing either the (R) or (S) enantiomer of a BOROX catalyst, a multicomponent reaction of this aldehyde with an amine and ethyl diazoacetate gives rise to enantiomeric aziridine-2-carboxylates. Access to all diastereomers of sphinganine is realized upon ring opening of the enantiopure aziridine-2-carboxylate at the C-3 position by direct SN2 attack of an oxygen nucleophile, which occurs with inversion of configuration and by ring expansion of an N-acyl aziridine to an oxazolidinone and then hydrolysis. Overall, this process results in the formal ring opening of the aziridine with an oxygen nucleophile with retention of configuration.
A general synthesis of sphinganines through multicomponent catalytic asymmetric aziridination
Mukherjee, Munmun,Zhou, Yubai,Gupta, Anil K.,Guan, Yong,Wulff, William D.
supporting information, p. 1386 - 1390 (2014/03/21)
A catalytic asymmetric synthesis of all four stereoisomers of sphinganine is described starting from hexadecanal. Utilizing either the (R) or (S) enantiomer of a BOROX catalyst, a multicomponent reaction of this aldehyde with an amine and ethyl diazoacetate gives rise to enantiomeric aziridine-2- carboxylates. Access to all diastereomers of sphinganine is realized upon ring opening of the enantiopure aziridine-2-carboxylate at the C-3 position by direct SN2 attack of an oxygen nucleophile, which occurs with inversion of configuration and by ring expansion of an N-acyl aziridine to an oxazolidinone and then hydrolysis. Overall, this process results in the formal ring opening of the aziridine with an oxygen nucleophile with retention of configuration. The synthesis of all four stereoisomers of sphinganine was achieved by multi-component asymmetric aziridination of hexadecanal. Complete stereocontrol is realized with the proper choice of the chirality of the BOROX catalyst and the introduction of an oxygen substituent at the 3-position of the aziridine with either retention or inversion. MEDAM = tetramethyldianisylmethyl. Copyright
Multicomponent catalytic asymmetric aziridination of aldehydes
Gupta, Anil K.,Mukherjee, Munmun,Wulff, William D.
supporting information; experimental part, p. 5866 - 5869 (2011/12/15)
The first multicomponent catalytic asymmetric aziridination reaction is developed to give aziridine-2-carboxylic esters with very high diastereo- and enantioselectivity from aromatic and aliphatic aldehydes. This new method pushes the boundary of the aziridination reaction to substrates that failed with preformed imines.
