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Highly stereoselective samarium(II) iodide-mediated aldol reactions of acylaziridines with aldehydes
The samarium(II) iodide-mediated stereoselective aldol reactions of acylaziridines with aldehydes are described. beta-Amino-beta?-hydroxy ketones were synthesized in high yields by the aldol reaction of aldehydes with samarium enolates generated by aziridine-fragmentation of aziridinyl ketones with two moles of samarium(II) iodide. By the choice of an appropriate nitrogen protecting group, depending on the substituent at C-3 position of aziridinyl ketone, anti,anti-beta-amino-beta?-hydroxy ketones were diastereoselectively obtained among the four possible diastereomers. Further, enantiomerically pure anti,anti-beta-amino-beta?-hydroxy ketones were successfully obtained by this aldol reaction when chiral aziridinyl ketones were used. In addition, delta-amino-?-hydroxy-beta,gamma-unsaturated esters were also synthesized in high yields by the aldol reaction of aldehydes with samarium enolates generated by aziridine-fragmentation and olefin-migration of gamma,delta-aziridinyl-alpha,beta-unsaturated esters using two moles of samarium(II) iodide. This aldol reaction proceeded with complete alpha-regioselectivity and formed (E)-olefin selectively. By introducing chiral oxazolidin-2-one auxiliary to gamma,delta-aziridinyl-alpha,beta- unsaturated carbonyl system, this reaction was extended successfully to the asymmetric reaction and enantiomerically pure syn-delta-amino-beta?- hydroxy-beta,gamma-unsaturated esters were obtained in high yields.
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Oxazolidine – Wikipedia,
Oxazolidine | C3H866NO – PubChem