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A versatile synthesis of unsymmetrical 3,3'-bioxindoles: stereoselective Mukaiyama aldol reactions of 2-siloxyindoles with isatins.
J Org Chem. 2008 Nov 21; 73(22):9151-4.JO

Abstract

A new synthesis of 3,3'-bioxindoles is reported that is well suited for the preparation of unsymmetrical structures. In the key step, 3-hydroxy-3,3'-bioxindoles are constructed by Mukaiyama aldol reaction of 2-siloxyindoles with isatins. These tertiary carbinols are formed in high diastereoselectivities, with substitution at various positions of the isatin and the 2-siloxyindole being tolerated.

Authors+Show Affiliations

Department of Chemistry, 1102 Natural Sciences II, University of California, Irvine, California 92697-2025, USA.No affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

Language

eng

PubMed ID

18855482

Citation

Ellis, J Michael, et al. "A Versatile Synthesis of Unsymmetrical 3,3'-bioxindoles: Stereoselective Mukaiyama Aldol Reactions of 2-siloxyindoles With Isatins." The Journal of Organic Chemistry, vol. 73, no. 22, 2008, pp. 9151-4.
Ellis JM, Overman LE, Tanner HR, et al. A versatile synthesis of unsymmetrical 3,3'-bioxindoles: stereoselective Mukaiyama aldol reactions of 2-siloxyindoles with isatins. J Org Chem. 2008;73(22):9151-4.
Ellis, J. M., Overman, L. E., Tanner, H. R., & Wang, J. (2008). A versatile synthesis of unsymmetrical 3,3'-bioxindoles: stereoselective Mukaiyama aldol reactions of 2-siloxyindoles with isatins. The Journal of Organic Chemistry, 73(22), 9151-4. https://doi.org/10.1021/jo801867w
Ellis JM, et al. A Versatile Synthesis of Unsymmetrical 3,3'-bioxindoles: Stereoselective Mukaiyama Aldol Reactions of 2-siloxyindoles With Isatins. J Org Chem. 2008 Nov 21;73(22):9151-4. PubMed PMID: 18855482.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - A versatile synthesis of unsymmetrical 3,3'-bioxindoles: stereoselective Mukaiyama aldol reactions of 2-siloxyindoles with isatins. AU - Ellis,J Michael, AU - Overman,Larry E, AU - Tanner,Huw R, AU - Wang,Jocelyn, Y1 - 2008/10/15/ PY - 2008/10/16/pubmed PY - 2009/1/10/medline PY - 2008/10/16/entrez SP - 9151 EP - 4 JF - The Journal of organic chemistry JO - J Org Chem VL - 73 IS - 22 N2 - A new synthesis of 3,3'-bioxindoles is reported that is well suited for the preparation of unsymmetrical structures. In the key step, 3-hydroxy-3,3'-bioxindoles are constructed by Mukaiyama aldol reaction of 2-siloxyindoles with isatins. These tertiary carbinols are formed in high diastereoselectivities, with substitution at various positions of the isatin and the 2-siloxyindole being tolerated. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/18855482/A_versatile_synthesis_of_unsymmetrical_33'_bioxindoles:_stereoselective_Mukaiyama_aldol_reactions_of_2_siloxyindoles_with_isatins_ L2 - https://doi.org/10.1021/jo801867w DB - PRIME DP - Unbound Medicine ER -