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Palladium-catalyzed synthesis of enantiomerically pure alpha-substituted allylboronic esters and their addition to aldehydes.
J Org Chem. 2010 Aug 20; 75(16):5580-9.JO

Abstract

Tartrate-derived boronic esters 2 can be subjected to palladium-catalyzed carbonyl allylations with SnCl(2) to obtain enantiomerically pure alpha-substituted allylboronic esters 8 and 9. The reaction proceeds regioselectively and with high, simple diastereoselectivity to form anti-products. Their addition to aldehydes yields enantiomerically enriched homoallylic alcohols 17 and 18, respectively. Synthesis, characterization, and a mechanistic rational is presented here.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Fernández E
Institut für Bioorganische Chemie der Heinrich-Heine-Universität Düsseldorf im Forschungszentrum Jülich, Germany.
Pietruszka J
No affiliation info available
Frey W
No affiliation info available

MeSH

AldehydesBoronic AcidsCatalysisCrystallography, X-RayEstersModels, MolecularMolecular ConformationOrganometallic CompoundsPalladiumStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

20672807

Citation

Fernández, Enrique, et al. "Palladium-catalyzed Synthesis of Enantiomerically Pure Alpha-substituted Allylboronic Esters and Their Addition to Aldehydes." The Journal of Organic Chemistry, vol. 75, no. 16, 2010, pp. 5580-9.
Fernández E, Pietruszka J, Frey W. Palladium-catalyzed synthesis of enantiomerically pure alpha-substituted allylboronic esters and their addition to aldehydes. J Org Chem. 2010;75(16):5580-9.
Fernández, E., Pietruszka, J., & Frey, W. (2010). Palladium-catalyzed synthesis of enantiomerically pure alpha-substituted allylboronic esters and their addition to aldehydes. The Journal of Organic Chemistry, 75(16), 5580-9. https://doi.org/10.1021/jo1008959
Fernández E, Pietruszka J, Frey W. Palladium-catalyzed Synthesis of Enantiomerically Pure Alpha-substituted Allylboronic Esters and Their Addition to Aldehydes. J Org Chem. 2010 Aug 20;75(16):5580-9. PubMed PMID: 20672807.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Palladium-catalyzed synthesis of enantiomerically pure alpha-substituted allylboronic esters and their addition to aldehydes. AU - Fernández,Enrique, AU - Pietruszka,Jörg, AU - Frey,Wolfgang, PY - 2010/8/3/entrez PY - 2010/8/3/pubmed PY - 2010/12/14/medline SP - 5580 EP - 9 JF - The Journal of organic chemistry JO - J Org Chem VL - 75 IS - 16 N2 - Tartrate-derived boronic esters 2 can be subjected to palladium-catalyzed carbonyl allylations with SnCl(2) to obtain enantiomerically pure alpha-substituted allylboronic esters 8 and 9. The reaction proceeds regioselectively and with high, simple diastereoselectivity to form anti-products. Their addition to aldehydes yields enantiomerically enriched homoallylic alcohols 17 and 18, respectively. Synthesis, characterization, and a mechanistic rational is presented here. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/20672807/Palladium_catalyzed_synthesis_of_enantiomerically_pure_alpha_substituted_allylboronic_esters_and_their_addition_to_aldehydes_ L2 - https://doi.org/10.1021/jo1008959 DB - PRIME DP - Unbound Medicine ER -