Synthesis of chiral N-phosphinyl α-imino esters and their application in asymmetric synthesis of α-amino esters by reduction

Yiwen Xiong; Haibo Mei; Lingmin Wu; Jianlin Han; Yi Pan; Guigen Li

doi:10.3762/bjoc.10.57

Synthesis of chiral N-phosphinyl α-imino esters and their application in asymmetric synthesis of α-amino esters by reduction

Yiwen Xiong, Haibo Mei, Lingmin Wu, Jianlin Han, Yi Pan, Guigen Li

Chemistry and Biochemistry

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

7 Scopus citations

Abstract

A variety of chiral N-phosphinyl a-imino esters have been synthesized for the first time from ketoesters and phosphinylamide, which were then reduced by L-selectride to give the corresponding N-phosphinyl-protected a-amino esters. The reduction proceeded very well with excellent chemical yields (88-98%) as well as high diastereoselectivities (96:4 to 99:1). Some of these products could be obtained without column chromatography and recrystallization. The chiral phosphinyl auxiliary could be easily cleaved under acidic conditions.

Original language	English
Pages (from-to)	653-659
Number of pages	7
Journal	Beilstein Journal of Organic Chemistry
Volume	10
DOIs	https://doi.org/10.3762/bjoc.10.57
State	Published - Mar 13 2014

Keywords

Group-assisted purification
Phosphinyl auxiliary
Reduction
α-amino ester
α-imino ester

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title = "Synthesis of chiral N-phosphinyl α-imino esters and their application in asymmetric synthesis of α-amino esters by reduction",

abstract = "A variety of chiral N-phosphinyl a-imino esters have been synthesized for the first time from ketoesters and phosphinylamide, which were then reduced by L-selectride to give the corresponding N-phosphinyl-protected a-amino esters. The reduction proceeded very well with excellent chemical yields (88-98%) as well as high diastereoselectivities (96:4 to 99:1). Some of these products could be obtained without column chromatography and recrystallization. The chiral phosphinyl auxiliary could be easily cleaved under acidic conditions.",

keywords = "Group-assisted purification, Phosphinyl auxiliary, Reduction, α-amino ester, α-imino ester",

author = "Yiwen Xiong and Haibo Mei and Lingmin Wu and Jianlin Han and Yi Pan and Guigen Li",

year = "2014",

month = mar,

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doi = "10.3762/bjoc.10.57",

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T1 - Synthesis of chiral N-phosphinyl α-imino esters and their application in asymmetric synthesis of α-amino esters by reduction

AU - Xiong, Yiwen

AU - Mei, Haibo

AU - Wu, Lingmin

AU - Han, Jianlin

AU - Pan, Yi

AU - Li, Guigen

PY - 2014/3/13

Y1 - 2014/3/13

N2 - A variety of chiral N-phosphinyl a-imino esters have been synthesized for the first time from ketoesters and phosphinylamide, which were then reduced by L-selectride to give the corresponding N-phosphinyl-protected a-amino esters. The reduction proceeded very well with excellent chemical yields (88-98%) as well as high diastereoselectivities (96:4 to 99:1). Some of these products could be obtained without column chromatography and recrystallization. The chiral phosphinyl auxiliary could be easily cleaved under acidic conditions.

AB - A variety of chiral N-phosphinyl a-imino esters have been synthesized for the first time from ketoesters and phosphinylamide, which were then reduced by L-selectride to give the corresponding N-phosphinyl-protected a-amino esters. The reduction proceeded very well with excellent chemical yields (88-98%) as well as high diastereoselectivities (96:4 to 99:1). Some of these products could be obtained without column chromatography and recrystallization. The chiral phosphinyl auxiliary could be easily cleaved under acidic conditions.

KW - Group-assisted purification

KW - Phosphinyl auxiliary

KW - Reduction

KW - α-amino ester

KW - α-imino ester

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DO - 10.3762/bjoc.10.57

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JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

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