Prev. Article Next Article Table of Contents

Letter

Catalytic Enantioselective Diels−Alder Reaction via a Chiral Indium(III) Complex

Supporting Info

Yong-Chua Teo^† and Teck-Peng Loh*^‡

Division of Chemistry and Biological Chemistry, Nanyang Technological University, Singapore 637616, and Department of Chemistry, 3 Science Drive, National University of Singapore, Singapore 117543

Org. Lett., 2005, 7 (13), pp 2539–2541

DOI: 10.1021/ol050518d

Publication Date (Web): June 1, 2005

†

National University of Singapore.

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

‡

Nanyang Technological University.

, teckpeng@ntu.edu.sg

Abstract

A chiral indium complex has been developed to effect high enantioselectivities in catalyzing enantioselective Diels−Alder reaction. The cycloaddition of a variety of cyclic and open-chained dienes to 2-methacrolein and 2-bromoacrolein resulted in good yields and excellent enantioselectivities (up to 98% ee).

View: Full Text HTML | Hi-Res PDF

Tools

SciFinder Links

History

Published In Issue June 23, 2005
Received March 9, 2005

Recommend & Share

Related Content

Asymmetric Diels−Alder Reactions Catalyzed by a Triflic Acid Activated Chiral OxazaborolidineJournal of the American Chemical Society
- Asymmetric Diels−Alder Reactions Catalyzed by a Triflic Acid Activated Chiral Oxazaborolidine
  E. J. Corey, Takanori Shibata, and Thomas W. Lee
  Journal of the American Chemical Society 2002 124 (15), pp 3808–3809
  Abstract: This paper reports a new method for the generation of chiral Lewis superacids by protonation of a non-Lewis acidic oxazaborolidine (1) with triflic acid. The resulting cationic species (3) are powerful and highly enantioselective catalysts for the Diels−...
  Abstract | Full Text HTML | Hi-Res PDF
Highly Enantioselective Allylation of Aldehydes Catalyzed by Indium(III)−PYBOX ComplexOrganic Letters
- Highly Enantioselective Allylation of Aldehydes Catalyzed by Indium(III)−PYBOX Complex
  Jun Lu, Shun-Jun Ji, Yong-Chua Teo, and Teck-Peng Loh
  Organic Letters 2005 7 (1), pp 159–161
  Abstract: A chiral indium(III)−PYBOX complex prepared from indium triflate and chiral PYBOX has been discovered to effect high enantioselectivities in the addition of allyltributyl stannane to aldehydes. The allylation of a variety of aromatic, α,β-unsaturated, and ...
  Abstract | Full Text HTML | Hi-Res PDF
The First General Enantioselective Catalytic Diels−Alder Reaction with Simple α,β-Unsaturated KetonesJournal of the American Chemical Society
- The First General Enantioselective Catalytic Diels−Alder Reaction with Simple α,β-Unsaturated Ketones
  Alan B. Northrup and David W. C. MacMillan
  Journal of the American Chemical Society 2002 124 (11), pp 2458–2460
  Abstract: The first general approach to enantioselective catalysis of the Diels−Alder reaction with simple ketone dienophiles has been accomplished. The use of iminium catalysis has enabled enantioselective access to a fundamental Diels−Alder reaction variant that ...
  Abstract | Full Text HTML | Hi-Res PDF

Letter

Catalytic Enantioselective Diels−Alder Reaction via a Chiral Indium(III) Complex

Abstract

Tools

SciFinder Links

History

Recommend & Share

Related Content

Asymmetric Diels−Alder Reactions Catalyzed by a Triflic Acid Activated Chiral Oxazaborolidine

Highly Enantioselective Allylation of Aldehydes Catalyzed by Indium(III)−PYBOX Complex

The First General Enantioselective Catalytic Diels−Alder Reaction with Simple α,β-Unsaturated Ketones

Other ACS content by these authors:

JOURNALS

BOOKS

MAGAZINE

COMMUNITIES

DIRECTORIES & DATABASES