Enantioselective trapping of phosphoramidate ammonium ylides with imino esters for synthesis of 2,3-diaminosuccinic acid derivatives

Jun Jiang; Xiaochu Ma; Shunying Liu; Yu Qian; Fengping Lv; Lin Qiu; Xiang Wu; Wenhao Hu

doi:10.1039/c3cc36972b

Enantioselective trapping of phosphoramidate ammonium ylides with imino esters for synthesis of 2,3-diaminosuccinic acid derivatives

Jun Jiang
, Xiaochu Ma
, Shunying Liu
, Yu Qian
, Fengping Lv
, Lin Qiu
, Xiang Wu
, Wenhao Hu^*

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

East China Normal University

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

52 Scopus citations

Abstract

A highly enantioselective trapping of protic phosphoramidate ammonium ylides with α-imino esters is reported. The intriguing Rh₂(OAc)₄ and chiral Brønsted acid co-catalyzed three-component Mannich-type reaction of a diazo compound, a phosphoramidate, and an α-imino ester provides a rapid and efficient access to 2,3-diaminosuccinic acid derivatives with a high level control of diastereo- and enantioselectivity.

Original language	English
Pages (from-to)	4238-4240
Number of pages	3
Journal	Chemical Communications
Volume	49
Issue number	39
DOIs	https://doi.org/10.1039/c3cc36972b
State	Published - 18 Apr 2013

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title = "Enantioselective trapping of phosphoramidate ammonium ylides with imino esters for synthesis of 2,3-diaminosuccinic acid derivatives",

abstract = "A highly enantioselective trapping of protic phosphoramidate ammonium ylides with α-imino esters is reported. The intriguing Rh2(OAc)4 and chiral Br{\o}nsted acid co-catalyzed three-component Mannich-type reaction of a diazo compound, a phosphoramidate, and an α-imino ester provides a rapid and efficient access to 2,3-diaminosuccinic acid derivatives with a high level control of diastereo- and enantioselectivity.",

author = "Jun Jiang and Xiaochu Ma and Shunying Liu and Yu Qian and Fengping Lv and Lin Qiu and Xiang Wu and Wenhao Hu",

year = "2013",

month = apr,

day = "18",

doi = "10.1039/c3cc36972b",

language = "英语",

volume = "49",

pages = "4238--4240",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

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TY - JOUR

T1 - Enantioselective trapping of phosphoramidate ammonium ylides with imino esters for synthesis of 2,3-diaminosuccinic acid derivatives

AU - Jiang, Jun

AU - Ma, Xiaochu

AU - Liu, Shunying

AU - Qian, Yu

AU - Lv, Fengping

AU - Qiu, Lin

AU - Wu, Xiang

AU - Hu, Wenhao

PY - 2013/4/18

Y1 - 2013/4/18

N2 - A highly enantioselective trapping of protic phosphoramidate ammonium ylides with α-imino esters is reported. The intriguing Rh2(OAc)4 and chiral Brønsted acid co-catalyzed three-component Mannich-type reaction of a diazo compound, a phosphoramidate, and an α-imino ester provides a rapid and efficient access to 2,3-diaminosuccinic acid derivatives with a high level control of diastereo- and enantioselectivity.

AB - A highly enantioselective trapping of protic phosphoramidate ammonium ylides with α-imino esters is reported. The intriguing Rh2(OAc)4 and chiral Brønsted acid co-catalyzed three-component Mannich-type reaction of a diazo compound, a phosphoramidate, and an α-imino ester provides a rapid and efficient access to 2,3-diaminosuccinic acid derivatives with a high level control of diastereo- and enantioselectivity.

UR - https://www.scopus.com/pages/publications/84876531023

U2 - 10.1039/c3cc36972b

DO - 10.1039/c3cc36972b

M3 - 文章

C2 - 23358554

AN - SCOPUS:84876531023

SN - 1359-7345

VL - 49

SP - 4238

EP - 4240

JO - Chemical Communications

JF - Chemical Communications

IS - 39

ER -

Enantioselective trapping of phosphoramidate ammonium ylides with imino esters for synthesis of 2,3-diaminosuccinic acid derivatives

Abstract

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