%0 Generic %A Burgo, Ander Vélez del %A M. Ochoa de Retana, Ana %A M. de los Santos, Jesús %A Palacios, Francisco %D 2016 %T Reaction of 2H‑Azirine-Phosphine Oxides and -Phosphonates with Enolates Derived from β‑Keto Esters %U https://acs.figshare.com/articles/dataset/Reaction_of_2_i_H_i_Azirine_Phosphine_Oxides_and_Phosphonates_with_Enolates_Derived_from_Keto_Esters/2092657 %R 10.1021/acs.joc.5b02347.s004 %2 https://acs.figshare.com/ndownloader/files/3725863 %K cyclic enolates %K C α %K carbonyl group %K vinylogou %K phosphine %K Enolates Derived %K oxide %K keto ester 10. Ring closure %X Cyclopenta­[b]-pyrrole-2-phosphine oxides 4a and -phosphonates 4b,c are generated by the addition of cyclic enolates derived from ethyl 2-oxo-cyclopentanecarboxylate 2 to phosphorated 2H-azirines 1. However, the addition of enolate derived from acyclic 2-oxo-butanoate 10 to 2H-azirine phosphine oxide 1 led to vinylogous N-acyl-α-aminoalkyl phosphine oxides 12, involving the carbonyl group and the Cα of the keto ester 10. Ring closure of vinylogous derivative 12 in the presence of base afforded pyrrole-2-phosphine oxide 11. The addition of enolates derived from indenone-carboxylate 15 to 2H-azirines 1 led to the formation of functionalized N-substituted 1H-benzo­[d]­azepine derivatives 17. %I ACS Publications