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Stereoselective Addition of Grignard Reagents to New P ‐Chirogenic N ‐Phosphinoylbenzaldimines: Effect of the Phosphorus Substituents on the Stereoselectivity
Author(s) -
Notar Francesco Irene,
Egloff Coraline,
Wagner Alain,
Colobert Françoise
Publication year - 2011
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.201100380
Subject(s) - diastereomer , chemistry , stereoselectivity , stereocenter , reagent , bromide , adduct , grignard reagent , phosphorus , medicinal chemistry , stereochemistry , organic chemistry , enantioselective synthesis , catalysis
Several phosphinoylimines have been synthesized in five steps by starting from the appropriate phosphane oxide and were then treated with methylmagnesium bromide to give both diastereoisomers in high yields and with promising diastereomeric ratios. Then N ‐[( tert ‐butyl)(phenyl)phosphinoyl]benzaldimine, which displayed the best results, was subjected to the 1,2‐addition of various Grignard reagents to evaluate the best chiral induction due to the stereogenic phosphorus atom. The corresponding adducts were obtained in excellent yields and with moderate to excellent diastereoisomeric ratios.