Prev. Article Next Article Table of Contents

Communication

Thiourea-Catalyzed Enantioselective Hydrophosphonylation of Imines: Practical Access to Enantiomerically Enriched α-Amino Phosphonic Acids

Supporting Info

Guy D. Joly and Eric N. Jacobsen*

Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138

J. Am. Chem. Soc., 2004, 126 (13), pp 4102–4103

DOI: 10.1021/ja0494398

Publication Date (Web): March 13, 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.

, jacobsen@chemistry.harvard.edu

Abstract

Chiral thiourea 1b catalyzes the highly enantioselective hydrophosphonylation of a wide range of N-benzyl imines. The hydrophosphonylation products are readily deprotected by hydrogenolysis, providing access to free α-amino phosphonic acids in highly enantioenriched form.

View: Full Text HTML | Hi-Res PDF

Tools

SciFinder Links

History

Published In Issue April 07, 2004
Received January 30, 2004

Recommend & Share

Related Content

Asymmetric Catalytic Mannich Reactions Catalyzed by Urea Derivatives: Enantioselective Synthesis of β-Aryl-β-Amino AcidsJournal of the American Chemical Society
- Asymmetric Catalytic Mannich Reactions Catalyzed by Urea Derivatives: Enantioselective Synthesis of β-Aryl-β-Amino Acids
  Anna G. Wenzel and Eric N. Jacobsen
  Journal of the American Chemical Society 2002 124 (44), pp 12964–12965
  Abstract: Highly enantioselective addition reactions between silyl ketene acetals and N-Boc aldimines are catalyzed by the thiourea-based catalyst 1c. Extraordinary scope is observed in this methodology with regard to the imine substrate, with aryl and ...
  Abstract | Full Text HTML | Hi-Res PDF
Highly Enantioselective Catalytic Acyl-Pictet−Spengler ReactionsJournal of the American Chemical Society
- Highly Enantioselective Catalytic Acyl-Pictet−Spengler Reactions
  Mark S. Taylor and Eric N. Jacobsen
  Journal of the American Chemical Society 2004 126 (34), pp 10558–10559
  Abstract: The enantioselective cyclization of N-acyliminium ions generated in situ from tryptamine is promoted with high enantioselectivity by a new chiral thiourea catalyst. This represents the first successful system for asymmetric catalysis of the Pictet−...
  Abstract | Full Text HTML | Hi-Res PDF
Thiourea-Catalyzed Enantioselective Cyanosilylation of KetonesJournal of the American Chemical Society
- Thiourea-Catalyzed Enantioselective Cyanosilylation of Ketones
  Douglas E. Fuerst and Eric N. Jacobsen
  Journal of the American Chemical Society 2005 127 (25), pp 8964–8965
  Abstract: The new chiral amino thiourea catalyst 3d promotes the highly enantioselective cyanosilylation of a wide variety of ketones. The hindered tertiary amine substituent plays a crucial role with regard to both stereoinduction and reactivity, suggesting a ...
  Abstract | Full Text HTML | Hi-Res PDF

Communication

Thiourea-Catalyzed Enantioselective Hydrophosphonylation of Imines: Practical Access to Enantiomerically Enriched α-Amino Phosphonic Acids

Abstract

Tools

SciFinder Links

History

Recommend & Share

Related Content

Asymmetric Catalytic Mannich Reactions Catalyzed by Urea Derivatives: Enantioselective Synthesis of β-Aryl-β-Amino Acids

Highly Enantioselective Catalytic Acyl-Pictet−Spengler Reactions

Thiourea-Catalyzed Enantioselective Cyanosilylation of Ketones

Other ACS content by these authors:

JOURNALS

BOOKS

MAGAZINE

COMMUNITIES

DIRECTORIES & DATABASES