Prev. Article Next Article Table of Contents

Communication

Asymmetric Synthesis of 3,3-Diarylpropanals with Chiral Diene−Rhodium Catalysts

Supporting Info

Jean-François Paquin, Christian Defieber, Corey R. J. Stephenson, and Erick M. Carreira*

Laboratorium fr Organische Chemie, ETH Hnggerberg, CH-8093 Zrich, Switzerland

J. Am. Chem. Soc., 2005, 127 (31), pp 10850–10851

DOI: 10.1021/ja053270w

Publication Date (Web): July 14, 2005

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

, carreira@org.chem.ethz.ch

Abstract

A general route to enantioenriched 3,3-diarylpropanals is presented. These useful building blocks are prepared via an asymmetric rhodium-catalyzed conjugate addition of arylboronic acids to cinnamaldehyde derivatives in the presence of chiral dienes. The addition of both electron-poor as well as electron-rich boronic acids proceeds smoothly with various enals in 63−90% yield with high enantioselectivities (89−93% ee).

View: Full Text HTML | Hi-Res PDF

Tools

SciFinder Links

History

Published In Issue August 10, 2005
Received May 19, 2005

Recommend & Share

Related Content

Catalytic Asymmetric Synthesis with Rh−Diene Complexes: 1,4-Addition of Arylboronic Acids to Unsaturated EstersOrganic Letters
- Catalytic Asymmetric Synthesis with Rh−Diene Complexes: 1,4-Addition of Arylboronic Acids to Unsaturated Esters
  Jean-François Paquin, Corey R. J. Stephenson, Christian Defieber, and Erick M. Carreira
  Organic Letters 2005 7 (17), pp 3821–3824
  Abstract: A general route to enantioenriched tert-butyl 3,3-diarylpropanoates is presented. These useful building blocks are prepared via an asymmetric rhodium-catalyzed conjugate addition of arylboronic acids to unsaturated tert-butyl esters in the presence of ...
  Abstract | Full Text HTML | Hi-Res PDF
Chiral [2.2.2] Dienes as Ligands for Rh(I) in Conjugate Additions of Boronic Acids to a Wide Range of AcceptorsOrganic Letters
- Chiral [2.2.2] Dienes as Ligands for Rh(I) in Conjugate Additions of Boronic Acids to a Wide Range of Acceptors
  Christian Defieber, Jean-François Paquin, Sonia Serna, and Erick M. Carreira
  Organic Letters 2004 6 (21), pp 3873–3876
  Abstract: We document a series of investigations that led to new substituted [2.2.2]-diene ligands which display high selectivity in Rh(I)-catalyzed conjugate addition reactions to substrates not previously examined with diene ligands. Moreover, we disclose an ...
  Abstract | Full Text HTML | Hi-Res PDF
Double Bond Isomerization/Enantioselective Aza-Petasis−Ferrier Rearrangement Sequence as an Efficient Entry to Anti- and Enantioenriched β-Amino AldehydesJournal of the American Chemical Society
- Double Bond Isomerization/Enantioselective Aza-Petasis−Ferrier Rearrangement Sequence as an Efficient Entry to Anti- and Enantioenriched β-Amino Aldehydes
  Masahiro Terada and Yasunori Toda
  Journal of the American Chemical Society 2009 131 (18), pp 6354–6355
  Abstract: Highly anti- and enantioselective synthesis of β-amino aldehydes having an aliphatic substituent at the β-position was accomplished by a combination of two catalytic reactions, that is, an initial Ni(II) complex-catalyzed isomerization of a double bond ...
  Abstract | Full Text HTML | PDF w/ Links | Hi-Res PDF

Communication

Asymmetric Synthesis of 3,3-Diarylpropanals with Chiral Diene−Rhodium Catalysts

Abstract

Tools

SciFinder Links

History

Recommend & Share

Related Content

Catalytic Asymmetric Synthesis with Rh−Diene Complexes: 1,4-Addition of Arylboronic Acids to Unsaturated Esters

Chiral [2.2.2] Dienes as Ligands for Rh(I) in Conjugate Additions of Boronic Acids to a Wide Range of Acceptors

Double Bond Isomerization/Enantioselective Aza-Petasis−Ferrier Rearrangement Sequence as an Efficient Entry to Anti- and Enantioenriched β-Amino Aldehydes

Other ACS content by these authors:

JOURNALS

BOOKS

MAGAZINE

COMMUNITIES

DIRECTORIES & DATABASES