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Asymmetric induction in the addition of enantiomerically pure H-phosphinate to chiral aldimines: diastereoselective generation of α-amino phosphinates with P, C-stereogenic centers. Issue 17 (1st October 2016)
Record Type:
Journal Article
Title:
Asymmetric induction in the addition of enantiomerically pure H-phosphinate to chiral aldimines: diastereoselective generation of α-amino phosphinates with P, C-stereogenic centers. Issue 17 (1st October 2016)
Main Title:
Asymmetric induction in the addition of enantiomerically pure H-phosphinate to chiral aldimines: diastereoselective generation of α-amino phosphinates with P, C-stereogenic centers
Graphical abstract: Abstract: α-Amino phosphinates with P, C -stereogenic centers were prepared from a P -retained addition of ( R P )-(−)-menthyl H -phenylphosphinate to ( R )-aldimines with up to 86:14 dr under catalyst and solvent free condition at ambient temperature; the single ( S P, S α-C )-stereoisomers were isolated in moderate yields. Chirality on the nitrogen of chiral aldimine was proposed to control the stereoselectivity, and the (−)-menthoxyl showed mismatched asymmetric induction with ( S )-aldimines.