Cyclization by Intramolecular Carbolithiation of Alkyl- and Vinyllithiums Prepared by the Action of Aromatic Radical Anions on Phenyl Thioethers. High Stereoselectivity in the Cyclization Accelerated by an Allylic Lithium Oxyanion1-Reference-Cited by-同舟云学术

Cyclization by Intramolecular Carbolithiation of Alkyl- and Vinyllithiums Prepared by the Action of Aromatic Radical Anions on Phenyl Thioethers. High Stereoselectivity in the Cyclization Accelerated by an Allylic Lithium Oxyanion1

Published:2006-02-24 Issue:6 Volume:71 Page:2360-2372
ISSN:0022-3263
Container-title:The Journal of Organic Chemistry
language:en
Short-container-title:J. Org. Chem.

Author:

Deng Kai¹,Bensari-Bouguerra Ahlem¹,Whetstone Joseph¹,Cohen Theodore¹

Affiliation:

1. Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260

Publisher

American Chemical Society (ACS)

Subject

Organic Chemistry

Link

https://pubs.acs.org/doi/pdf/10.1021/jo052535m

Reference56 articles.

1. Taken in part from the Ph.D. thesis of Kai Deng: Deng, K. Ph.D. Thesis, University of Pittsburgh, 2004.

2. (a) Reviews: Bailey, W. F.; Ovaska, T. V. InAdvancesinDetailedReactionMechanisms; Coxon, J. M., Ed.; JAI Press: Greenwich, CT; 1994; Vol. 3, pp 251−273. Mealy, M. J.; Bailey, W. F.J.Organomet.Chem.2002,646, 59−67. Clayden, J.Organolithiums:SelectivityforSynthesis; Pergamon Press: New York, 2002; pp 293−335. Marek, I.; Chinkov, N.; Banon-Tenne, D. InMetal-CatalyzedCross-CouplingReactions, 2n ed.; de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, Germany, 2004; Vol. 1, pp 395−478. Recent papers: (b) Bailey, W. F.; Jiang, X. L.Tetrahedron2005,61, 3183−3194.

3. Intramolecular carbolithiation reactions for the preparation of 3-alkenylpyrrolidines

4. Stereoselectivity of cyclization of substituted 5-hexen-1-yllithiums: regiospecific and highly stereoselective insertion of an unactivated alkene into a carbon-lithium bond

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