Orthogonally protected Schöllkopf’s bis-lactim ethers for the asymmetric synthesis of α-amino acid derivatives and dipeptide esters

Marc Hutchby; Adam C Sedgwick; Steven D. Bull

doi:10.1055/s-0035-1561943

Orthogonally protected Schöllkopf’s bis-lactim ethers for the asymmetric synthesis of α-amino acid derivatives and dipeptide esters

Marc Hutchby, Adam C Sedgwick, Steven D. Bull

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

10 Citations (SciVal)

Abstract

Alkylation of the aza-enolates of orthogonally protected chiral bis-lactim ethers with electrophiles proceeds with good levels of diastereocontrol to afford trans-alkylated adducts that can be efficiently deprotected via hydrolysis/hydrogenation procedures to afford non-proteinogenic α-amino acid or dipeptide ester derivatives.

Original language	English
Pages (from-to)	2036-2049
Journal	Synthesis
Volume	48
Issue number	13
Early online date	26 Apr 2016
DOIs	https://doi.org/10.1055/s-0035-1561943
Publication status	Published - Jul 2016

Access to Document

10.1055/s-0035-1561943

Cite this

@article{85c4d46e0fb04d66a5b6a71a1c4447ed,

title = "Orthogonally protected Sch{\"o}llkopf{\textquoteright}s bis-lactim ethers for the asymmetric synthesis of α-amino acid derivatives and dipeptide esters",

abstract = "Alkylation of the aza-enolates of orthogonally protected chiral bis-lactim ethers with electrophiles proceeds with good levels of diastereocontrol to afford trans-alkylated adducts that can be efficiently deprotected via hydrolysis/hydrogenation procedures to afford non-proteinogenic α-amino acid or dipeptide ester derivatives.",

author = "Marc Hutchby and Sedgwick, \{Adam C\} and Bull, \{Steven D.\}",

year = "2016",

month = jul,

doi = "10.1055/s-0035-1561943",

language = "English",

volume = "48",

pages = "2036--2049",

journal = "Synthesis",

issn = "0039-7881",

publisher = "Georg Thieme Verlag",

number = "13",

}

TY - JOUR

T1 - Orthogonally protected Schöllkopf’s bis-lactim ethers for the asymmetric synthesis of α-amino acid derivatives and dipeptide esters

AU - Hutchby, Marc

AU - Sedgwick, Adam C

AU - Bull, Steven D.

PY - 2016/7

Y1 - 2016/7

N2 - Alkylation of the aza-enolates of orthogonally protected chiral bis-lactim ethers with electrophiles proceeds with good levels of diastereocontrol to afford trans-alkylated adducts that can be efficiently deprotected via hydrolysis/hydrogenation procedures to afford non-proteinogenic α-amino acid or dipeptide ester derivatives.

AB - Alkylation of the aza-enolates of orthogonally protected chiral bis-lactim ethers with electrophiles proceeds with good levels of diastereocontrol to afford trans-alkylated adducts that can be efficiently deprotected via hydrolysis/hydrogenation procedures to afford non-proteinogenic α-amino acid or dipeptide ester derivatives.

UR - http://dx.doi.org/10.1055/s-0035-1561943

UR - https://www.scopus.com/pages/publications/84992311229

U2 - 10.1055/s-0035-1561943

DO - 10.1055/s-0035-1561943

M3 - Article

SN - 0039-7881

VL - 48

SP - 2036

EP - 2049

JO - Synthesis

JF - Synthesis

IS - 13

ER -

Orthogonally protected Schöllkopf’s bis-lactim ethers for the asymmetric synthesis of α-amino acid derivatives and dipeptide esters

Abstract

Access to Document

Other files and links

Fingerprint

Electrospray Time-of-Flight Mass Spectrometer (Open-Access)

Cite this

Orthogonally protected Schöllkopf’s bis-lactim ethers for the asymmetric synthesis of α-amino acid derivatives and dipeptide esters

Abstract

Access to Document

Other files and links

Fingerprint

Equipment

Electrospray Time-of-Flight Mass Spectrometer (Open-Access)

Cite this