Tags

Type your tag names separated by a space and hit enter

Stereochemical surprises in the Lewis acid-mediated allylation of isatins.
J Org Chem. 2010 Oct 01; 75(19):6720-3.JO

Abstract

The BF(3)·OEt(2)-mediated allylation of isatin with an α-chiral allylic stannane is diastereo- and enantioselective. Conversely, allylation of any substituted isatin employing the identical protocol is not diastereoselective at all and only enantioselective for the major diastereomer having syn relative configuration. The anti isomer is, however, formed in almost racemic form. Both absolute and relative configurations are unambiguously secured by X-ray analysis of major isomers, and the stereochemical assignment of the other 3-substituted 3-hydroxy oxindoles is based on similar NMR spectroscopic characteristics. The remarkable observations are rationalized by an acyclic transition state model.

Authors+Show Affiliations

Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, 48149 Münster, Germany.No affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

20825233

Citation

Vyas, Devendra J., et al. "Stereochemical Surprises in the Lewis Acid-mediated Allylation of Isatins." The Journal of Organic Chemistry, vol. 75, no. 19, 2010, pp. 6720-3.
Vyas DJ, Fröhlich R, Oestreich M. Stereochemical surprises in the Lewis acid-mediated allylation of isatins. J Org Chem. 2010;75(19):6720-3.
Vyas, D. J., Fröhlich, R., & Oestreich, M. (2010). Stereochemical surprises in the Lewis acid-mediated allylation of isatins. The Journal of Organic Chemistry, 75(19), 6720-3. https://doi.org/10.1021/jo101420e
Vyas DJ, Fröhlich R, Oestreich M. Stereochemical Surprises in the Lewis Acid-mediated Allylation of Isatins. J Org Chem. 2010 Oct 1;75(19):6720-3. PubMed PMID: 20825233.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Stereochemical surprises in the Lewis acid-mediated allylation of isatins. AU - Vyas,Devendra J, AU - Fröhlich,Roland, AU - Oestreich,Martin, PY - 2010/9/10/entrez PY - 2010/9/10/pubmed PY - 2011/1/5/medline SP - 6720 EP - 3 JF - The Journal of organic chemistry JO - J Org Chem VL - 75 IS - 19 N2 - The BF(3)·OEt(2)-mediated allylation of isatin with an α-chiral allylic stannane is diastereo- and enantioselective. Conversely, allylation of any substituted isatin employing the identical protocol is not diastereoselective at all and only enantioselective for the major diastereomer having syn relative configuration. The anti isomer is, however, formed in almost racemic form. Both absolute and relative configurations are unambiguously secured by X-ray analysis of major isomers, and the stereochemical assignment of the other 3-substituted 3-hydroxy oxindoles is based on similar NMR spectroscopic characteristics. The remarkable observations are rationalized by an acyclic transition state model. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/20825233/Stereochemical_surprises_in_the_Lewis_acid_mediated_allylation_of_isatins_ L2 - https://doi.org/10.1021/jo101420e DB - PRIME DP - Unbound Medicine ER -