%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