Prev. Article Next Article Table of Contents

Article

A Novel Class of Tunable Zinc Reagents (RXZnCH₂Y) for Efficient Cyclopropanation of Olefins

Jon C. Lorenz,^† Jiang Long,^† Zhiqiang Yang,^† Song Xue, Yinong Xie, and Yian Shi*

Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523

J. Org. Chem., 2004, 69 (2), pp 327–334

DOI: 10.1021/jo030312v

Publication Date (Web): December 17, 2003

†

J.C.L., J.L., and Z.Y. contributed equally to this work.

Phone: 970-491-7424. Fax: 970-491-1801.

, yian@lamar.colostate.edu

Abstract

A class of zinc reagents (RXZnCH₂Y) generated with an appropriate organozinc is very effective for the cyclopropanation of olefins. The reactivity and selectivity of these reagents can be regulated by tuning the electronic and steric nature of the RX group on Zn. A reasonable level of enantioselectivity was obtained for the cyclopropanation of unfunctionalized olefins when a chiral (iodomethyl)zinc species was used, providing a valuable approach for the asymmetric cyclopropanation of unfunctionalized olefins.

View: Full Text HTML | Hi-Res PDF

Tools

SciFinder Links

History

Published In Issue January 23, 2004
Received October 10, 2003

Recommend & Share

Related Content

Stereoselective Cyclopropanation ReactionsChemical Reviews
- Stereoselective Cyclopropanation Reactions
  Hélène Lebel, Jean-François Marcoux, Carmela Molinaro, and André B. Charette
  Chemical Reviews 2003 103 (4), pp 977–1050
  Abstract | Full Text HTML | Hi-Res PDF
A comparison of (chloromethyl)- and (iodomethyl)zinc cyclopropanation reagentsThe Journal of Organic Chemistry
- A comparison of (chloromethyl)- and (iodomethyl)zinc cyclopropanation reagents
  Scott E. Denmark, James P. Edwards
  The Journal of Organic Chemistry 1991 56 (25), pp 6974–6981
  Abstract | Hi-Res PDF
Catalytic Asymmetric Simmons−Smith Cyclopropanation of Silyl Enol Ethers. Efficient Synthesis of Optically Active Cyclopropanol DerivativesOrganic Letters
- Catalytic Asymmetric Simmons−Smith Cyclopropanation of Silyl Enol Ethers. Efficient Synthesis of Optically Active Cyclopropanol Derivatives
  Haifeng Du, Jiang Long, and Yian Shi
  Organic Letters 2006 8 (13), pp 2827–2829
  Abstract: This paper describes a catalytic asymmetric Simmons−Smith cyclopropanation of silyl enol ethers using dipeptide 2 as the ligand. A variety of optically active cyclopropyl silyl ethers can be obtained in high yields. Up to 96% ee was obtained. The ...
  Abstract | Full Text HTML | Hi-Res PDF

Article

A Novel Class of Tunable Zinc Reagents (RXZnCH₂Y) for Efficient Cyclopropanation of Olefins