Electrophilic amination of ketone enolates mediated by the DiTOX asymmetric building block: Enantioselective formal synthesis of alpha-aminoacids

Philip C.. Bulman Page; Michael J. McKenzie; Steven M. Allin; Derek R. Buckle

doi:10.1016/S0040-4020(00)00923-6

Electrophilic amination of ketone enolates mediated by the DiTOX asymmetric building block: Enantioselective formal synthesis of alpha-aminoacids

Philip C.. Bulman Page
, Michael J. McKenzie
, Steven M. Allin
, Derek R. Buckle

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

25 Citations (Scopus)

Abstract

Diastereoselective electrophilic amination of enolates derived from 2-acyl-1,3-dithiane 1-oxides is used as the key step for an enantioselective synthesis of two alpha -hydrazido carboxylic acids, well-known precursors of alpha -amino acids. (C) 2000 Elsevier Science Ltd. All rights reserved.

Original language	English
Pages (from-to)	9683-9695
Number of pages	13
Journal	Tetrahedron
Volume	56
Issue number	49
DOIs	https://doi.org/10.1016/S0040-4020(00)00923-6
Publication status	Published - 2000

Keywords

ARYLGLYCINES
ETHERS
ALKYLATION
SULFOXIDATION
ESTERS
HYDRAZINO ACIDS
chiral auxiliary
3-DITHIANE 1-OXIDES
ACID-DERIVATIVES
1
asymmetric synthesis
aminoacid
STEREOSELECTIVE AMINATION
enolate
AZODICARBOXYLATE

Access to Document

10.1016/S0040-4020(00)00923-6

Cite this

@article{dac0ed8586094128856f2254ee4be95d,

title = "Electrophilic amination of ketone enolates mediated by the DiTOX asymmetric building block: Enantioselective formal synthesis of alpha-aminoacids",

abstract = "Diastereoselective electrophilic amination of enolates derived from 2-acyl-1,3-dithiane 1-oxides is used as the key step for an enantioselective synthesis of two alpha -hydrazido carboxylic acids, well-known precursors of alpha -amino acids. (C) 2000 Elsevier Science Ltd. All rights reserved.",

keywords = "ARYLGLYCINES, ETHERS, ALKYLATION, SULFOXIDATION, ESTERS, HYDRAZINO ACIDS, chiral auxiliary, 3-DITHIANE 1-OXIDES, ACID-DERIVATIVES, 1, asymmetric synthesis, aminoacid, STEREOSELECTIVE AMINATION, enolate, AZODICARBOXYLATE",

author = "\{Bulman Page\}, \{Philip C..\} and McKenzie, \{Michael J.\} and Allin, \{Steven M.\} and Buckle, \{Derek R.\}",

year = "2000",

doi = "10.1016/S0040-4020(00)00923-6",

language = "English",

volume = "56",

pages = "9683--9695",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier",

number = "49",

}

TY - JOUR

T1 - Electrophilic amination of ketone enolates mediated by the DiTOX asymmetric building block: Enantioselective formal synthesis of alpha-aminoacids

AU - Bulman Page, Philip C..

AU - McKenzie, Michael J.

AU - Allin, Steven M.

AU - Buckle, Derek R.

PY - 2000

Y1 - 2000

N2 - Diastereoselective electrophilic amination of enolates derived from 2-acyl-1,3-dithiane 1-oxides is used as the key step for an enantioselective synthesis of two alpha -hydrazido carboxylic acids, well-known precursors of alpha -amino acids. (C) 2000 Elsevier Science Ltd. All rights reserved.

AB - Diastereoselective electrophilic amination of enolates derived from 2-acyl-1,3-dithiane 1-oxides is used as the key step for an enantioselective synthesis of two alpha -hydrazido carboxylic acids, well-known precursors of alpha -amino acids. (C) 2000 Elsevier Science Ltd. All rights reserved.

KW - ARYLGLYCINES

KW - ETHERS

KW - ALKYLATION

KW - SULFOXIDATION

KW - ESTERS

KW - HYDRAZINO ACIDS

KW - chiral auxiliary

KW - 3-DITHIANE 1-OXIDES

KW - ACID-DERIVATIVES

KW - 1

KW - asymmetric synthesis

KW - aminoacid

KW - STEREOSELECTIVE AMINATION

KW - enolate

KW - AZODICARBOXYLATE

U2 - 10.1016/S0040-4020(00)00923-6

DO - 10.1016/S0040-4020(00)00923-6

M3 - Article

SN - 0040-4020

VL - 56

SP - 9683

EP - 9695

JO - Tetrahedron

JF - Tetrahedron

IS - 49

ER -