Prev. Article Next Article Table of Contents

Letter

Stereochemical Control of the Passerini Reaction

Supporting Info

Peter R. Andreana, Chang C. Liu, and Stuart L. Schreiber*

Howard Hughes Medical Institute, Center for Chemical Methodology and Library Development (CMLD-HU) & Broad Institute of Harvard and MIT, Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138

Org. Lett., 2004, 6 (23), pp 4231–4233

DOI: 10.1021/ol0482893

Publication Date (Web): October 12, 2004

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

, stuart_schreiber@harvard.edu

Abstract

A catalytic asymmetric Passerini reaction using tridentate indan (pybox) Cu(II) Lewis acid complex 4 with substrates capable of bidentate coordination has been achieved. The reaction occurs via ligand-accelerated catalysis.

View: Full Text HTML | Hi-Res PDF

Tools

SciFinder Links

History

Published In Issue November 11, 2004
Received August 26, 2004

Recommend & Share

Related Content

Massive Parallel Catalyst Screening: Toward Asymmetric MCRsOrganic Letters
- Massive Parallel Catalyst Screening: Toward Asymmetric MCRs
  Ulrike Kusebauch, Barbara Beck, Kim Messer, Eberhardt Herdtweck, and Alexander Dömling
  Organic Letters 2003 5 (22), pp 4021–4024
  Abstract: Hundreds of Lewis acid/ligand combinations have been screened for stereochemical induction in the Passerini multicomponent reaction. The combination of titan tetraisopropylate and (4S,5S)-4,5-bis(diphenylhydroxymethyl)-2,2-dimethyldioxolane was found to ...
  Abstract | Full Text HTML | Hi-Res PDF
The First Catalytic, Asymmetric α-Additions of Isocyanides. Lewis-Base-Catalyzed, Enantioselective Passerini-Type ReactionsJournal of the American Chemical Society
- The First Catalytic, Asymmetric α-Additions of Isocyanides. Lewis-Base-Catalyzed, Enantioselective Passerini-Type Reactions
  Scott E. Denmark and Yu Fan
  Journal of the American Chemical Society 2003 125 (26), pp 7825–7827
  Abstract: The first, catalytic, enantioselective α-additions of isocyanides to aldehydes have been demonstrated (Passerini-type reactions). The catalytic system of silicon tetrachloride and a chiral bisphosphoramide 5a provided high yields and good to excellent ...
  Abstract | Full Text HTML | Hi-Res PDF
Metal-Promoted Variants of the Passerini Reaction Leading to Functionalized HeterocyclesOrganic Letters
- Metal-Promoted Variants of the Passerini Reaction Leading to Functionalized Heterocycles
  Qian Xia and Bruce Ganem
  Organic Letters 2002 4 (9), pp 1631–1634
  Abstract: The effect of replacing the Brønsted acid in classic Passerini reactions with a mild Lewis acid has been studied. Triggered by metal-promoted silylation, condensations of aliphatic or aromatic carbonyl compounds with appropriately substituted isonitriles ...
  Abstract | Full Text HTML | Hi-Res PDF

Letter

Stereochemical Control of the Passerini Reaction

Abstract

Tools

SciFinder Links

History

Recommend & Share

Related Content

Massive Parallel Catalyst Screening: Toward Asymmetric MCRs

The First Catalytic, Asymmetric α-Additions of Isocyanides. Lewis-Base-Catalyzed, Enantioselective Passerini-Type Reactions

Metal-Promoted Variants of the Passerini Reaction Leading to Functionalized Heterocycles

Other ACS content by these authors:

JOURNALS

BOOKS

MAGAZINE

COMMUNITIES

DIRECTORIES & DATABASES