Enantiodiscrimination of racemic electrophiles by diketopiperazine enolates: asymmetric synthesis of 3-methyl aspartates and methyl 2-amino-3-aryl-butanoates

S D Bull; S G Davies; S W Epstein; A C Garner; N Mujtaba; E D Savory; Andrew David Smith; J A Tamayo; D J Watkin

doi:10.1016/j.tet.2006.05.033

Enantiodiscrimination of racemic electrophiles by diketopiperazine enolates: asymmetric synthesis of 3-methyl aspartates and methyl 2-amino-3-aryl-butanoates

S D Bull, S G Davies, S W Epstein, A C Garner, N Mujtaba, E D Savory, Andrew David Smith, J A Tamayo, D J Watkin

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

27 Citations (Scopus)

Abstract

Enolates of (S)-N,N'-bis-(p-methoxybenzyl)-3-iso-propylpiperazine-2,5-dione exhibit high levels of enantiodiscrimination in alkylations with (RS)-1-aryl-1-bromoethanes and (RS)-2-bromoesters, affording substituted diketopiperazines containing two new stereogenic centres in high de. Deprotection and hydrolysis of the resultant substituted diketopiperazines provides a route to the asymmetric synthesis of homochiral methyl 2-amino-3-aryl-butanoates and 3-methyl-aspartates in high de and ee. (c) 2006 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	7911
Number of pages	7911
Journal	Tetrahedron
Volume	62
DOIs	https://doi.org/10.1016/j.tet.2006.05.033
Publication status	Published - 14 Aug 2006

Keywords

enantiodiscrimination
diketopiperazine
3-methyl-aspartate
ALPHA-AMINO-ACIDS
ANTIMITOTIC BICYCLIC PEPTIDES
MAXIMUM OPTICAL ROTATIONS
CHIRAL RELAY AUXILIARY
KINETIC RESOLUTION
STEREOSELECTIVE-SYNTHESIS
3-ALKYLALKANOIC ACIDS
CONJUGATE ADDITIONS
OXIDATIVE ADDITION
CELOSIA-ARGENTEA

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10.1016/j.tet.2006.05.033

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title = "Enantiodiscrimination of racemic electrophiles by diketopiperazine enolates: asymmetric synthesis of 3-methyl aspartates and methyl 2-amino-3-aryl-butanoates",

abstract = "Enolates of (S)-N,N'-bis-(p-methoxybenzyl)-3-iso-propylpiperazine-2,5-dione exhibit high levels of enantiodiscrimination in alkylations with (RS)-1-aryl-1-bromoethanes and (RS)-2-bromoesters, affording substituted diketopiperazines containing two new stereogenic centres in high de. Deprotection and hydrolysis of the resultant substituted diketopiperazines provides a route to the asymmetric synthesis of homochiral methyl 2-amino-3-aryl-butanoates and 3-methyl-aspartates in high de and ee. (c) 2006 Elsevier Ltd. All rights reserved.",

keywords = "enantiodiscrimination, diketopiperazine, 3-methyl-aspartate, ALPHA-AMINO-ACIDS, ANTIMITOTIC BICYCLIC PEPTIDES, MAXIMUM OPTICAL ROTATIONS, CHIRAL RELAY AUXILIARY, KINETIC RESOLUTION, STEREOSELECTIVE-SYNTHESIS, 3-ALKYLALKANOIC ACIDS, CONJUGATE ADDITIONS, OXIDATIVE ADDITION, CELOSIA-ARGENTEA",

author = "Bull, {S D} and Davies, {S G} and Epstein, {S W} and Garner, {A C} and N Mujtaba and Savory, {E D} and Smith, {Andrew David} and Tamayo, {J A} and Watkin, {D J}",

year = "2006",

month = aug,

day = "14",

doi = "10.1016/j.tet.2006.05.033",

language = "English",

volume = "62",

pages = "7911",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier",

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T1 - Enantiodiscrimination of racemic electrophiles by diketopiperazine enolates: asymmetric synthesis of 3-methyl aspartates and methyl 2-amino-3-aryl-butanoates

AU - Bull, S D

AU - Davies, S G

AU - Epstein, S W

AU - Garner, A C

AU - Mujtaba, N

AU - Savory, E D

AU - Smith, Andrew David

AU - Tamayo, J A

AU - Watkin, D J

PY - 2006/8/14

Y1 - 2006/8/14

N2 - Enolates of (S)-N,N'-bis-(p-methoxybenzyl)-3-iso-propylpiperazine-2,5-dione exhibit high levels of enantiodiscrimination in alkylations with (RS)-1-aryl-1-bromoethanes and (RS)-2-bromoesters, affording substituted diketopiperazines containing two new stereogenic centres in high de. Deprotection and hydrolysis of the resultant substituted diketopiperazines provides a route to the asymmetric synthesis of homochiral methyl 2-amino-3-aryl-butanoates and 3-methyl-aspartates in high de and ee. (c) 2006 Elsevier Ltd. All rights reserved.

AB - Enolates of (S)-N,N'-bis-(p-methoxybenzyl)-3-iso-propylpiperazine-2,5-dione exhibit high levels of enantiodiscrimination in alkylations with (RS)-1-aryl-1-bromoethanes and (RS)-2-bromoesters, affording substituted diketopiperazines containing two new stereogenic centres in high de. Deprotection and hydrolysis of the resultant substituted diketopiperazines provides a route to the asymmetric synthesis of homochiral methyl 2-amino-3-aryl-butanoates and 3-methyl-aspartates in high de and ee. (c) 2006 Elsevier Ltd. All rights reserved.

KW - enantiodiscrimination

KW - diketopiperazine

KW - 3-methyl-aspartate

KW - ALPHA-AMINO-ACIDS

KW - ANTIMITOTIC BICYCLIC PEPTIDES

KW - MAXIMUM OPTICAL ROTATIONS

KW - CHIRAL RELAY AUXILIARY

KW - KINETIC RESOLUTION

KW - STEREOSELECTIVE-SYNTHESIS

KW - 3-ALKYLALKANOIC ACIDS

KW - CONJUGATE ADDITIONS

KW - OXIDATIVE ADDITION

KW - CELOSIA-ARGENTEA

UR - http://www.scopus.com/inward/record.url?scp=33745713078&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2006.05.033

DO - 10.1016/j.tet.2006.05.033

M3 - Article

SN - 0040-4020

VL - 62

SP - 7911

JO - Tetrahedron

JF - Tetrahedron

ER -

Enantiodiscrimination of racemic electrophiles by diketopiperazine enolates: asymmetric synthesis of 3-methyl aspartates and methyl 2-amino-3-aryl-butanoates

Abstract

Keywords

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