Efficient asymmetric synthesis of P-chiral phosphine oxides via properly designed and activated benzoxazaphosphinine-2-oxide agents.
A general, efficient, and highly diastereoselective method for the synthesis of structurally and sterically diverse P-chiral phosphine oxides was developed. The method relies on sequential nucleophilic substitution on the versatile chiral phosphinyl transfer agent 1,3,2-benzoxazaphosphinine-2-oxide, which features enhanced and differentiated P-N and P-O bond reactivity toward nucleophiles. The reactivities of both bonds are fine-tuned to allow cleavage to occur even with sterically hindered nucleophiles under mild conditions.
Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals Inc., 900 Old Ridgebury Road, P.O. Box 368, Ridgefield, Connecticut 06877, USA. steve.han@boehringer-ingelheim.com
Zhengxu S
ZS
Han
Navneet
N
Goyal
Melissa A
MA
Herbage
Joshua D
JD
Sieber
Bo
B
Qu
Yibo
Y
Xu
Zhibin
Z
Li
Jonathan T
JT
Reeves
Jean-Nicolas
JN
Desrosiers
Shengli
S
Ma
Nelu
N
Grinberg
Heewon
H
Lee
Hari P R
HP
Mangunuru
Yongda
Y
Zhang
Dhileep
D
Krishnamurthy
Bruce Z
BZ
Lu
Jinhua J
JJ
Song
Guijun
G
Wang
Chris H
CH
Senanayake
D003498:Cyclic P-Oxides / Q000138:chemical synthesis* / Q000737:chemistry; D008024:Ligands; D015394:Molecular Structure; D010720:Phosphines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D003498:Cyclic P-Oxides; D008024:Ligands; D010720:Phosphines; C044646:phosphine