Organocatalytic enantioselective direct vinylogous michael addition of α,β-unsaturated γ-butyrolactam to β-acyl acrylates and 1,2-diacylethylenes

Yi Ru Chen, Utpal Das, Meng Hsien Liu, Wenwei Lin

Research output: Contribution to journal › Article

29 Citations (Scopus)

Abstract

A highly efficient Michael addition of α,β-unsaturated γ-butyrolactam to various β-acyl acrylates and ene-diones to provide synthetically useful compounds was developed. The products were obtained with high diastereo- and enantioselectivities (up to >25:1 dr and 99% ee) containing adjacent tertiary stereocenters.

Original languageEnglish
Pages (from-to)1985-1992
Number of pages8
JournalJournal of Organic Chemistry
Volume80
Issue number3
DOIs
Publication statusPublished - 2015 Feb 6

Fingerprint

Acrylates
Enantioselectivity

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Organocatalytic enantioselective direct vinylogous michael addition of α,β-unsaturated γ-butyrolactam to β-acyl acrylates and 1,2-diacylethylenes. / Chen, Yi Ru; Das, Utpal; Liu, Meng Hsien; Lin, Wenwei.

In: Journal of Organic Chemistry, Vol. 80, No. 3, 06.02.2015, p. 1985-1992.

Research output: Contribution to journal › Article

Chen, YR, Das, U, Liu, MH & Lin, W 2015, 'Organocatalytic enantioselective direct vinylogous michael addition of α,β-unsaturated γ-butyrolactam to β-acyl acrylates and 1,2-diacylethylenes', Journal of Organic Chemistry, vol. 80, no. 3, pp. 1985-1992. https://doi.org/10.1021/jo5027047
Chen YR, Das U, Liu MH, Lin W. Organocatalytic enantioselective direct vinylogous michael addition of α,β-unsaturated γ-butyrolactam to β-acyl acrylates and 1,2-diacylethylenes. Journal of Organic Chemistry. 2015 Feb 6;80(3):1985-1992. https://doi.org/10.1021/jo5027047
Chen, Yi Ru ; Das, Utpal ; Liu, Meng Hsien ; Lin, Wenwei. / Organocatalytic enantioselective direct vinylogous michael addition of α,β-unsaturated γ-butyrolactam to β-acyl acrylates and 1,2-diacylethylenes. In: Journal of Organic Chemistry. 2015 ; Vol. 80, No. 3. pp. 1985-1992.
@article{88222b67ad3640d7ae912dafd83e2c9d,
title = "Organocatalytic enantioselective direct vinylogous michael addition of α,β-unsaturated γ-butyrolactam to β-acyl acrylates and 1,2-diacylethylenes",
abstract = "A highly efficient Michael addition of α,β-unsaturated γ-butyrolactam to various β-acyl acrylates and ene-diones to provide synthetically useful compounds was developed. The products were obtained with high diastereo- and enantioselectivities (up to >25:1 dr and 99{\%} ee) containing adjacent tertiary stereocenters.",
author = "Chen, {Yi Ru} and Utpal Das and Liu, {Meng Hsien} and Wenwei Lin",
year = "2015",
month = "2",
day = "6",
doi = "10.1021/jo5027047",
language = "English",
volume = "80",
pages = "1985--1992",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "3",

}

TY - JOUR

T1 - Organocatalytic enantioselective direct vinylogous michael addition of α,β-unsaturated γ-butyrolactam to β-acyl acrylates and 1,2-diacylethylenes

AU - Chen, Yi Ru

AU - Das, Utpal

AU - Liu, Meng Hsien

AU - Lin, Wenwei

PY - 2015/2/6

Y1 - 2015/2/6

N2 - A highly efficient Michael addition of α,β-unsaturated γ-butyrolactam to various β-acyl acrylates and ene-diones to provide synthetically useful compounds was developed. The products were obtained with high diastereo- and enantioselectivities (up to >25:1 dr and 99% ee) containing adjacent tertiary stereocenters.

AB - A highly efficient Michael addition of α,β-unsaturated γ-butyrolactam to various β-acyl acrylates and ene-diones to provide synthetically useful compounds was developed. The products were obtained with high diastereo- and enantioselectivities (up to >25:1 dr and 99% ee) containing adjacent tertiary stereocenters.

UR - http://www.scopus.com/inward/record.url?scp=84922712502&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84922712502&partnerID=8YFLogxK

U2 - 10.1021/jo5027047

DO - 10.1021/jo5027047

M3 - Article

C2 - 25562697

AN - SCOPUS:84922712502

VL - 80

SP - 1985

EP - 1992

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 3

ER -

Access to Document