Catalytic enantioselective addition of diethyl phosphite to N-thiophosphinoyl ketimines: Preparation of (R)-diethyl (1-amino-1-phenylethyl)phosphonate

Shaoquan Lin; Yasunari Otsuka; Liang Yin; Naoya Kumagai; Masakatsu Shibasaki

doi:10.1002/0471264229.os094.23

Catalytic enantioselective addition of diethyl phosphite to N-thiophosphinoyl ketimines: Preparation of (R)-diethyl (1-amino-1-phenylethyl)phosphonate

Shaoquan Lin, Yasunari Otsuka, Liang Yin, Naoya Kumagai, Masakatsu Shibasaki

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

1 Citation (Scopus)

Abstract

Procedures yielding phosphinothioic amide 2 and ketimine 4 as colorless crystals and phosphonate 6 as a brown viscous oil are presented. Notes on instruments and chemicals required are provided.A brief discussion on construction of tetrasubstituted stereogenic centers in a catalytic and enantioselective manner as a significant progress in asymmetric catalysis.

Original language	English
Journal	Organic Syntheses
Volume	94
DOIs	https://doi.org/10.1002/0471264229.os094.23
Publication status	Published - 2018 Jun 20
Externally published	Yes

Keywords

Ceric ammonium molybdate
Chlorodiphenylphosphine
Diethyl phosphate
Dimethyl fumarate
Enantioselective
N-hexane
Phosphinothioic amide

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

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10.1002/0471264229.os094.23

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title = "Catalytic enantioselective addition of diethyl phosphite to N-thiophosphinoyl ketimines: Preparation of (R)-diethyl (1-amino-1-phenylethyl)phosphonate",

abstract = "Procedures yielding phosphinothioic amide 2 and ketimine 4 as colorless crystals and phosphonate 6 as a brown viscous oil are presented. Notes on instruments and chemicals required are provided.A brief discussion on construction of tetrasubstituted stereogenic centers in a catalytic and enantioselective manner as a significant progress in asymmetric catalysis.",

keywords = "Ceric ammonium molybdate, Chlorodiphenylphosphine, Diethyl phosphate, Dimethyl fumarate, Enantioselective, N-hexane, Phosphinothioic amide",

author = "Shaoquan Lin and Yasunari Otsuka and Liang Yin and Naoya Kumagai and Masakatsu Shibasaki",

year = "2018",

month = jun,

day = "20",

doi = "10.1002/0471264229.os094.23",

language = "English",

volume = "94",

journal = "Organic Syntheses",

issn = "0078-6209",

publisher = "John Wiley and Sons Inc.",

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TY - JOUR

T1 - Catalytic enantioselective addition of diethyl phosphite to N-thiophosphinoyl ketimines

T2 - Preparation of (R)-diethyl (1-amino-1-phenylethyl)phosphonate

AU - Lin, Shaoquan

AU - Otsuka, Yasunari

AU - Yin, Liang

AU - Kumagai, Naoya

AU - Shibasaki, Masakatsu

PY - 2018/6/20

Y1 - 2018/6/20

N2 - Procedures yielding phosphinothioic amide 2 and ketimine 4 as colorless crystals and phosphonate 6 as a brown viscous oil are presented. Notes on instruments and chemicals required are provided.A brief discussion on construction of tetrasubstituted stereogenic centers in a catalytic and enantioselective manner as a significant progress in asymmetric catalysis.

AB - Procedures yielding phosphinothioic amide 2 and ketimine 4 as colorless crystals and phosphonate 6 as a brown viscous oil are presented. Notes on instruments and chemicals required are provided.A brief discussion on construction of tetrasubstituted stereogenic centers in a catalytic and enantioselective manner as a significant progress in asymmetric catalysis.

KW - Ceric ammonium molybdate

KW - Chlorodiphenylphosphine

KW - Diethyl phosphate

KW - Dimethyl fumarate

KW - Enantioselective

KW - N-hexane

KW - Phosphinothioic amide

UR - http://www.scopus.com/inward/record.url?scp=85054798937&partnerID=8YFLogxK

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U2 - 10.1002/0471264229.os094.23

DO - 10.1002/0471264229.os094.23

M3 - Article

AN - SCOPUS:85054798937

VL - 94

JO - Organic Syntheses

JF - Organic Syntheses

SN - 0078-6209

ER -

Catalytic enantioselective addition of diethyl phosphite to N-thiophosphinoyl ketimines: Preparation of (R)-diethyl (1-amino-1-phenylethyl)phosphonate

Abstract

Keywords

ASJC Scopus subject areas

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