A novel conformationally restricted analogue of 3-methylaspartic acid via stereoselective methylation of chiral pyrrolidin-2-ones

Emanuela Crucianelli, Roberta Galeazzi, Gianluca Martelli, Mario Orena, Samuele Rinaldi, Piera Sabatino

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

Conformationally restricted analogues of β-methylaspartic acid were easily prepared starting from chiral N-protected trans-3-amino-4-methoxycarbonyl pyrrolidin-2-ones. The key step of the synthesis was the methylation reaction at C-4, proceeding with high diastereoselection syn to the protected amino group lying at C-3 of the pyrrolidin-2-one ring.

Original languageEnglish
Pages (from-to)400-405
Number of pages6
JournalTetrahedron
Volume66
Issue number1
DOIs
Publication statusPublished - Jan 2 2010

Fingerprint

Methylation
Acids
3-methylaspartic acid

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

A novel conformationally restricted analogue of 3-methylaspartic acid via stereoselective methylation of chiral pyrrolidin-2-ones. / Crucianelli, Emanuela; Galeazzi, Roberta; Martelli, Gianluca; Orena, Mario; Rinaldi, Samuele; Sabatino, Piera.

In: Tetrahedron, Vol. 66, No. 1, 02.01.2010, p. 400-405.

Research output: Contribution to journalArticle

Crucianelli, Emanuela ; Galeazzi, Roberta ; Martelli, Gianluca ; Orena, Mario ; Rinaldi, Samuele ; Sabatino, Piera. / A novel conformationally restricted analogue of 3-methylaspartic acid via stereoselective methylation of chiral pyrrolidin-2-ones. In: Tetrahedron. 2010 ; Vol. 66, No. 1. pp. 400-405.
@article{b7d49ea5c1ea4ae2a664b9c4ab8e596c,
title = "A novel conformationally restricted analogue of 3-methylaspartic acid via stereoselective methylation of chiral pyrrolidin-2-ones",
abstract = "Conformationally restricted analogues of β-methylaspartic acid were easily prepared starting from chiral N-protected trans-3-amino-4-methoxycarbonyl pyrrolidin-2-ones. The key step of the synthesis was the methylation reaction at C-4, proceeding with high diastereoselection syn to the protected amino group lying at C-3 of the pyrrolidin-2-one ring.",
author = "Emanuela Crucianelli and Roberta Galeazzi and Gianluca Martelli and Mario Orena and Samuele Rinaldi and Piera Sabatino",
year = "2010",
month = "1",
day = "2",
doi = "10.1016/j.tet.2009.10.004",
language = "English",
volume = "66",
pages = "400--405",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "1",

}

TY - JOUR

T1 - A novel conformationally restricted analogue of 3-methylaspartic acid via stereoselective methylation of chiral pyrrolidin-2-ones

AU - Crucianelli, Emanuela

AU - Galeazzi, Roberta

AU - Martelli, Gianluca

AU - Orena, Mario

AU - Rinaldi, Samuele

AU - Sabatino, Piera

PY - 2010/1/2

Y1 - 2010/1/2

N2 - Conformationally restricted analogues of β-methylaspartic acid were easily prepared starting from chiral N-protected trans-3-amino-4-methoxycarbonyl pyrrolidin-2-ones. The key step of the synthesis was the methylation reaction at C-4, proceeding with high diastereoselection syn to the protected amino group lying at C-3 of the pyrrolidin-2-one ring.

AB - Conformationally restricted analogues of β-methylaspartic acid were easily prepared starting from chiral N-protected trans-3-amino-4-methoxycarbonyl pyrrolidin-2-ones. The key step of the synthesis was the methylation reaction at C-4, proceeding with high diastereoselection syn to the protected amino group lying at C-3 of the pyrrolidin-2-one ring.

UR - http://www.scopus.com/inward/record.url?scp=70549096003&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=70549096003&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2009.10.004

DO - 10.1016/j.tet.2009.10.004

M3 - Article

AN - SCOPUS:70549096003

VL - 66

SP - 400

EP - 405

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 1

ER -