Alkylation of Imidazolidinone Dipeptide Derivatives: Preparation of Enantiomerically Pure Di‐ and Tripeptides by ‘Chirality Transfer’ via a Pivalaldehyde N,N‐Acetal Center. Preliminary Communication

Robin L Polt, Dieter Seebach

Research output: Contribution to journalArticle

26 Citations (Scopus)

Abstract

Glycylglycine, glycyl‐(S)‐alanine, and (S)‐alanylglycine esters are cyclized through pivalaldehyde imines to give dipeptide‐derived 3‐(benzyloxycarbonyl)‐2‐(tert‐butyl)‐5‐oxoimidazolidine‐1‐acetates 1–3. These are alkylated diastereoselectively by Li‐enolate formation and addition of alkyl bromides or iodides (products 4–6). Starting from (S)‐alanine and glycine, (S)‐alanyl‐(S)‐alanine or (R)‐alanyl‐(R)‐alanine, and (R)‐alanyl‐(R)alanyl‐(S)‐alanine‐ have thus been prepared, with the (tert‐butyl)‐substituted N,N‐acetal center playing the role of a pivot or lever for diastereoselective formation of new stereogenic centers under kinetic or thermodynamic control.

Original languageEnglish (US)
Pages (from-to)1930-1936
Number of pages7
JournalHelvetica Chimica Acta
Volume70
Issue number7
DOIs
StatePublished - 1987
Externally publishedYes

Fingerprint

Dipeptides
Chirality
alkylation
Alkylation
alanine
chirality
Alanine
Amino acids
Esters
communication
Thermodynamics
Derivatives
preparation
Kinetics
Communication
N-glycylalanine
alanylglycine
Glycylglycine
Imines
Iodides

ASJC Scopus subject areas

  • Catalysis
  • Biochemistry
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

Cite this

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title = "Alkylation of Imidazolidinone Dipeptide Derivatives: Preparation of Enantiomerically Pure Di‐ and Tripeptides by ‘Chirality Transfer’ via a Pivalaldehyde N,N‐Acetal Center. Preliminary Communication",
abstract = "Glycylglycine, glycyl‐(S)‐alanine, and (S)‐alanylglycine esters are cyclized through pivalaldehyde imines to give dipeptide‐derived 3‐(benzyloxycarbonyl)‐2‐(tert‐butyl)‐5‐oxoimidazolidine‐1‐acetates 1–3. These are alkylated diastereoselectively by Li‐enolate formation and addition of alkyl bromides or iodides (products 4–6). Starting from (S)‐alanine and glycine, (S)‐alanyl‐(S)‐alanine or (R)‐alanyl‐(R)‐alanine, and (R)‐alanyl‐(R)alanyl‐(S)‐alanine‐ have thus been prepared, with the (tert‐butyl)‐substituted N,N‐acetal center playing the role of a pivot or lever for diastereoselective formation of new stereogenic centers under kinetic or thermodynamic control.",
author = "Polt, {Robin L} and Dieter Seebach",
year = "1987",
doi = "10.1002/hlca.19870700727",
language = "English (US)",
volume = "70",
pages = "1930--1936",
journal = "Helvetica Chimica Acta",
issn = "0018-019X",
publisher = "Verlag Helvetica Chimica Acta AG",
number = "7",

}

TY - JOUR

T1 - Alkylation of Imidazolidinone Dipeptide Derivatives

T2 - Preparation of Enantiomerically Pure Di‐ and Tripeptides by ‘Chirality Transfer’ via a Pivalaldehyde N,N‐Acetal Center. Preliminary Communication

AU - Polt, Robin L

AU - Seebach, Dieter

PY - 1987

Y1 - 1987

N2 - Glycylglycine, glycyl‐(S)‐alanine, and (S)‐alanylglycine esters are cyclized through pivalaldehyde imines to give dipeptide‐derived 3‐(benzyloxycarbonyl)‐2‐(tert‐butyl)‐5‐oxoimidazolidine‐1‐acetates 1–3. These are alkylated diastereoselectively by Li‐enolate formation and addition of alkyl bromides or iodides (products 4–6). Starting from (S)‐alanine and glycine, (S)‐alanyl‐(S)‐alanine or (R)‐alanyl‐(R)‐alanine, and (R)‐alanyl‐(R)alanyl‐(S)‐alanine‐ have thus been prepared, with the (tert‐butyl)‐substituted N,N‐acetal center playing the role of a pivot or lever for diastereoselective formation of new stereogenic centers under kinetic or thermodynamic control.

AB - Glycylglycine, glycyl‐(S)‐alanine, and (S)‐alanylglycine esters are cyclized through pivalaldehyde imines to give dipeptide‐derived 3‐(benzyloxycarbonyl)‐2‐(tert‐butyl)‐5‐oxoimidazolidine‐1‐acetates 1–3. These are alkylated diastereoselectively by Li‐enolate formation and addition of alkyl bromides or iodides (products 4–6). Starting from (S)‐alanine and glycine, (S)‐alanyl‐(S)‐alanine or (R)‐alanyl‐(R)‐alanine, and (R)‐alanyl‐(R)alanyl‐(S)‐alanine‐ have thus been prepared, with the (tert‐butyl)‐substituted N,N‐acetal center playing the role of a pivot or lever for diastereoselective formation of new stereogenic centers under kinetic or thermodynamic control.

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DO - 10.1002/hlca.19870700727

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EP - 1936

JO - Helvetica Chimica Acta

JF - Helvetica Chimica Acta

SN - 0018-019X

IS - 7

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