Chiral N-phosphonyl imine chemistry: Asymmetric additions of glycine enolate to diphenyl diamine-based phosphonyl imines

Teng Ai; Suresh Pindi; Padmanabha V. Kattamuri; Guigen Li

doi:10.1007/s11426-010-0026-y

Chiral N-phosphonyl imine chemistry: Asymmetric additions of glycine enolate to diphenyl diamine-based phosphonyl imines

Teng Ai, Suresh Pindi, Padmanabha V. Kattamuri, Guigen Li

Center for Drug Design

Research output: Contribution to journal › Article › peer-review

17 Scopus citations

Abstract

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.

Original language	English (US)
Pages (from-to)	125-129
Number of pages	5
Journal	Science China Chemistry
Volume	53
Issue number	1
DOIs	https://doi.org/10.1007/s11426-010-0026-y
State	Published - Jan 2010

Bibliographical note

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)

Copyright:
Copyright 2010 Elsevier B.V., All rights reserved.

Keywords

Chiral N-phosphonyl imine
Chiral phosphoramide
Glycine enolate
α-β diamino ester

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10.1007/s11426-010-0026-y

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abstract = "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.",

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author = "Teng Ai and Suresh Pindi and Kattamuri, {Padmanabha V.} and Guigen Li",

note = "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) Copyright: Copyright 2010 Elsevier B.V., All rights reserved.",

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doi = "10.1007/s11426-010-0026-y",

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T2 - Asymmetric additions of glycine enolate to diphenyl diamine-based phosphonyl imines

AU - Ai, Teng

AU - Pindi, Suresh

AU - Kattamuri, Padmanabha V.

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) Copyright: Copyright 2010 Elsevier B.V., All rights reserved.

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

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Chiral N-phosphonyl imine chemistry: Asymmetric additions of glycine enolate to diphenyl diamine-based phosphonyl imines

Abstract

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