1,3-dipolar cycloadditions of carbonyl ylides to aldimines: scope, limitations and asymmetric...

2007 Hydroxycarboxylic acids (ether carboxylic acids) and esters Q 0450 1,3-Dipolar Cycloadditions of Carbonyl Ylides to Aldimines: Scope, Limitations and Asymmetric Cycloadditions. — A three-component approach for the highly dia- stereoselective synthesis of syn-α-hydroxy-β-amino esters involves the Rh-catalyzed 1,3-dipolar cycloaddition of carbonyl ylides, generated in situ, to imines.The use of chiral α-methylbenzylimines (IV) as dipolarophiles is a promising approach to an asymmetric version (up to 80% diastereoselectivity). Another possibility is the use of Rh 2 ((S)-DOSP) 4 (up to 64% e.e.). — (TORSSELL, S.; SOMFAI*, P.; Adv. Synth. Catal. 348 (2006) 16-17, 2421-2430; KTH Chem. Sci. Eng., Org. Chem., R. Inst. Technol., S-100 44 Stockholm, Swed.; Eng.) — Mischke 12- 088

Upload: staffan-torssell

Post on 11-Jun-2016

217 views

Category:

Documents

0 download

Report

Download

Embed Size (px):

TRANSCRIPT

Page 1: 1,3-Dipolar Cycloadditions of Carbonyl Ylides to Aldimines: Scope, Limitations and Asymmetric Cycloadditions

2007

Hydroxycarboxylic acids (ether carboxylic acids) and estersQ 0450 1,3-Dipolar Cycloadditions of Carbonyl Ylides to Aldimines: Scope, Limitations

and Asymmetric Cycloadditions. — A three-component approach for the highly dia-stereoselective synthesis of syn-α-hydroxy-β-amino esters involves the Rh-catalyzed 1,3-dipolar cycloaddition of carbonyl ylides, generated in situ, to imines.The use of chiral α-methylbenzylimines (IV) as dipolarophiles is a promising approach to an asymmetric version (up to 80% diastereoselectivity). Another possibility is the use of Rh2((S)-DOSP)4 (up to 64% e.e.). — (TORSSELL, S.; SOMFAI*, P.; Adv. Synth. Catal. 348 (2006) 16-17, 2421-2430; KTH Chem. Sci. Eng., Org. Chem., R. Inst. Technol., S-100 44 Stockholm, Swed.; Eng.) — Mischke

12- 088

33 [2+1]-cycloadditions

31 [3+2]-cycloadditions

Asymmetric 1,3-Dipolar Cycloaddition of Azomethine ylides

Asymmetric [4+3] Cycloadditions between Vinylcarbenoidsand … · 2009. 7. 8. · Asymmetric [4+3] Cycloadditions between Vinylcarbenoidsand Dienes: Application to the Total Synthesis

use in 1,3-dipolar cycloadditions to form nitrogen ... · use in 1,3-dipolar cycloadditions to form nitrogen-containing polyaromatic hydrocarbons Shingo Ito*, Yuki Tokimaru and Kyoko

Organic Photoredox-Catalyzed Cycloadditions Under Single

Strain-Promoted Alkyne-Nitrone Cycloadditions: Developing

Nickel-Catalyzed Cycloadditions - Princeton University · Nickel-Catalyzed Cycloadditions Tristan Lambert MacMillan Group Meeting January 31, 2001 Properties of nickel Introduction

Syntheses and Cycloadditions of Novel Nitrones

Interconversion of Nitrenes, Carbenes and Nitrile Ylides ... · Interconversion of Nitrenes, Carbenes and Nitrile Ylides by Ring Expansion, Ring Opening, Ring Contraction, and Ring

PHOSPHORUS AND SULPHUR YLIDES · The Chemistry of Phosphorus and Sulphur Ylides 2 A ylide or ylid is a neutral dipolar molecule containing a formally negatively charged atom (usually