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Access to 1‐Phospha‐2‐azanorbornenes by Phospha‐aza‐Diels–Alder Reactions
Author(s) -
Wonneberger Peter,
König Nils,
Kraft Fabian B.,
Sárosi Menyhárt B.,
HeyHawkins Evamarie
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201811673
Subject(s) - chemistry , imine , diels–alder reaction , nucleophile , medicinal chemistry , photochemistry , computational chemistry , organic chemistry , catalysis
The unprecedented phospha‐aza‐Diels–Alder reaction between an activated electron‐poor imine and 2 H ‐phospholes yields 1‐phospha‐2‐azanorbornenes in a highly chemoselective and moderately diastereoselective reaction. The intermediate 2 H ‐phospholes, which act as dienes, are formed in situ from the corresponding 1 H ‐phospholes. Theoretical calculations confirm that the phospha‐aza‐Diels–Alder reaction is of normal electron demand. The reactive P−N bond in 1‐phospha‐2‐azanorbornenes can be cleaved by nucleophiles leading to the formation of 2,3‐dihydrophospholes.