TY - JOUR
T1 - Chiral N-phosphonyl imine chemistry: asymmetric additions of glycine enolate to diphenyl diamine-based phosphonyl imines
T2 - Asymmetric additions of glycine enolate to diphenyl diamine-based phosphonyl imines
AU - Ai, Teng
AU - Pindi, Suresh
AU - Kattamuri, Padmanabha
AU - Li, Guigen
N1 - Funding Information:
This work was supported by the National Institutes of Health (Grant Nos. 1 RO3 DA026960-01), and Robert Welch Foundation (Grant No. D-1361)
PY - 2010/1
Y1 - 2010/1
N2 - Diphenyl diamine-based phosphonyl imines attached by the N-isopropyl group in the auxiliary have been synthesized in good yields under convenient reaction conditions. These new chiral N-phosphonyl imines can react with glycine enolate smoothly to give chiral α-β diamino esters in good yields (72%-90%) and up to excellent diastereoselectivity (>99:1 dr). By treatment with HBr, the chiral auxiliary can be readily removed. The absolute structure has been unambiguously determined by converting a product to a known sample.
AB - Diphenyl diamine-based phosphonyl imines attached by the N-isopropyl group in the auxiliary have been synthesized in good yields under convenient reaction conditions. These new chiral N-phosphonyl imines can react with glycine enolate smoothly to give chiral α-β diamino esters in good yields (72%-90%) and up to excellent diastereoselectivity (>99:1 dr). By treatment with HBr, the chiral auxiliary can be readily removed. The absolute structure has been unambiguously determined by converting a product to a known sample.
KW - Chiral N-phosphonyl imine
KW - Chiral phosphoramide
KW - Glycine enolate
KW - α-β diamino ester
UR - http://www.scopus.com/inward/record.url?scp=76449114361&partnerID=8YFLogxK
U2 - 10.1007/s11426-010-0026-y
DO - 10.1007/s11426-010-0026-y
M3 - Article
SN - 1674-7291
VL - 53
SP - 125
EP - 129
JO - Science China-Chemistry
JF - Science China-Chemistry
IS - 1
ER -