Premium
Phosphane‐Catalyzed [3+2] Annulation of Allenoates with 3‐Nitro‐2 H ‐chromenes: Synthesis of Tetrahydrocyclopenta[ c ]chromenes
Author(s) -
Soares Maria I. L.,
Gomes Clara S. B.,
Nunes Sandra C. C.,
Pais Alberto A. C. C.,
Pinho e Melo Teresa M. V. D.
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900564
Subject(s) - annulation , chemistry , allene , regioselectivity , nitro , trichlorosilane , catalysis , selectivity , organic chemistry , medicinal chemistry , stereochemistry , alkyl , silicon
The synthesis of carbocyclic‐fused chromene derivatives based on allene chemistry is described. The phosphane‐catalyzed [3+2] annulation reactions of allenic esters with 3‐nitrochromenes have been established affording 3a‐nitro‐tetrahydrocyclopenta[ c ]chromenes in good yields (up to 87 %) with high stereo‐ and regioselectivity. Quantum chemical calculations, carried out at the DFT level of theory, were in agreement with the observed selectivity. The trichlorosilane‐mediated reduction of the 3a‐nitro‐tetrahydrocyclopenta[ c ]chromenes into the corresponding amines is also reported.