Organocatalytic Asymmetric Synthesis of Propargylamines with Two Adjacent Stereocenters: Mannich-Type Reactions of In Situ Generated C-Alkynyl Imines with β-Keto Esters

Side by side: The title reaction is catalyzed by the chiral Brønsted acid (S)‐1, and affords hitherto less accessible chiral propargylamines, having two adjacent stereocenters, in good to excellent diastereo‐ and enantioselectivities. Boc=tert‐butoxycarbonyl.

Saved in:
Bibliographic Details
Published in:Angewandte Chemie (International ed.) 2013-10, Vol.52 (44), p.11509-11512
Main Authors: Kano, Taichi, Yurino, Taiga, Maruoka, Keiji
Format: Article
Language:English
Subjects:
amines
asymmetric catalysis
Catalysis
Esters
imines
Imines - chemical synthesis
Imines - chemistry
Models, Molecular
Molecular Structure
organocatalysis
Pargyline - analogs & derivatives
Pargyline - chemical synthesis
Pargyline - chemistry
Propylamines - chemical synthesis
Propylamines - chemistry
Stereoisomerism
synthetic methods
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Side by side: The title reaction is catalyzed by the chiral Brønsted acid (S)‐1, and affords hitherto less accessible chiral propargylamines, having two adjacent stereocenters, in good to excellent diastereo‐ and enantioselectivities. Boc=tert‐butoxycarbonyl.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201304963