Enantioselective organocatalytic conjugate addition of amines to α,β-unsaturated aldehydes: one-pot asymmetric synthesis of β-amino acids and 1,3-diamines

Jan Vesely; Ismail Ibrahem; Ramon Rios; Gui Ling Zhao; Yongmei Xu; Armando Córdova

doi:10.1016/j.tetlet.2007.01.093

Enantioselective organocatalytic conjugate addition of amines to α,β-unsaturated aldehydes: one-pot asymmetric synthesis of β-amino acids and 1,3-diamines

Jan Vesely
, Ismail Ibrahem
, Ramon Rios
, Gui Ling Zhao
, Yongmei Xu
, Armando Córdova

Chemistry

Arrhenius Laboratory

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

111 Scopus citations

Abstract

Organocatalytic asymmetric amine conjugate additions to α,β-unsaturated aldehydes catalyzed by protected diarylprolinols are presented. The reactions proceed with high enantioselectivity and result in Cbz or Boc protected β-amino aldehydes, γ-amino alcohols, β-amino acids and 1,3-diamines with typically 82-99% ee.

Original language	British English
Pages (from-to)	2193-2198
Number of pages	6
Journal	Tetrahedron Letters
Volume	48
Issue number	12
DOIs	https://doi.org/10.1016/j.tetlet.2007.01.093
State	Published - 19 Mar 2007

Access to Document

10.1016/j.tetlet.2007.01.093

OpenUrl availability

Full text

Cite this

@article{36004ca577ea4932b16c396c1db405c2,

title = "Enantioselective organocatalytic conjugate addition of amines to α,β-unsaturated aldehydes: one-pot asymmetric synthesis of β-amino acids and 1,3-diamines",

abstract = "Organocatalytic asymmetric amine conjugate additions to α,β-unsaturated aldehydes catalyzed by protected diarylprolinols are presented. The reactions proceed with high enantioselectivity and result in Cbz or Boc protected β-amino aldehydes, γ-amino alcohols, β-amino acids and 1,3-diamines with typically 82-99\% ee.",

author = "Jan Vesely and Ismail Ibrahem and Ramon Rios and Zhao, \{Gui Ling\} and Yongmei Xu and Armando C{\'o}rdova",

note = "Funding Information: We gratefully acknowledge the Swedish National Research Council and Carl-Trygger Foundation for financial support. ",

year = "2007",

month = mar,

day = "19",

doi = "10.1016/j.tetlet.2007.01.093",

language = "British English",

volume = "48",

pages = "2193--2198",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd",

number = "12",

}

TY - JOUR

T1 - Enantioselective organocatalytic conjugate addition of amines to α,β-unsaturated aldehydes

T2 - one-pot asymmetric synthesis of β-amino acids and 1,3-diamines

AU - Vesely, Jan

AU - Ibrahem, Ismail

AU - Rios, Ramon

AU - Zhao, Gui Ling

AU - Xu, Yongmei

AU - Córdova, Armando

N1 - Funding Information: We gratefully acknowledge the Swedish National Research Council and Carl-Trygger Foundation for financial support.

PY - 2007/3/19

Y1 - 2007/3/19

N2 - Organocatalytic asymmetric amine conjugate additions to α,β-unsaturated aldehydes catalyzed by protected diarylprolinols are presented. The reactions proceed with high enantioselectivity and result in Cbz or Boc protected β-amino aldehydes, γ-amino alcohols, β-amino acids and 1,3-diamines with typically 82-99% ee.

AB - Organocatalytic asymmetric amine conjugate additions to α,β-unsaturated aldehydes catalyzed by protected diarylprolinols are presented. The reactions proceed with high enantioselectivity and result in Cbz or Boc protected β-amino aldehydes, γ-amino alcohols, β-amino acids and 1,3-diamines with typically 82-99% ee.

UR - https://www.scopus.com/pages/publications/33847029577

U2 - 10.1016/j.tetlet.2007.01.093

DO - 10.1016/j.tetlet.2007.01.093

M3 - Article

AN - SCOPUS:33847029577

SN - 0040-4039

VL - 48

SP - 2193

EP - 2198

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 12

ER -

Enantioselective organocatalytic conjugate addition of amines to α,β-unsaturated aldehydes: one-pot asymmetric synthesis of β-amino acids and 1,3-diamines

Abstract

Access to Document

OpenUrl availability

Other files and links

Fingerprint

Cite this