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Predicting the stereochemistry of diphenylphosphino benzoic acid (DPPBA)-based palladium-catalyzed asymmetric allylic alkylation reactions: a working model.
Acc Chem Res. 2006 Oct; 39(10):747-60.AC

Abstract

Palladium-catalyzed asymmetric allylic alkylation has proven to be a powerful method for the preparation of a wide variety of chiral compounds and the rapid assembly of complex molecular architecture from simple starting materials. While many types of catalyst systems have been successfully employed with certain systems, diphenylphosphino benzoic acid (DPPBA) based ligands have found use over a broad range of substrate classes. This Account highlights the mechanistic aspects considered when designing reactions with DPPBA-based ligands and presents a working model for the a priori prediction of their stereochemical outcome.

Authors+Show Affiliations

Trost BM
Department of Chemistry, Stanford University, Stanford, CA 94305-5080, USA. bmtrost@stanford.edu
Machacek MR
No affiliation info available
Aponick A
No affiliation info available

MeSH

AlkylationAllyl CompoundsBenzamidesCatalysisLigandsModels, ChemicalMolecular ConformationPalladiumPhosphinesStereoisomerism

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

17042475

Citation

Trost, Barry M., et al. "Predicting the Stereochemistry of Diphenylphosphino Benzoic Acid (DPPBA)-based Palladium-catalyzed Asymmetric Allylic Alkylation Reactions: a Working Model." Accounts of Chemical Research, vol. 39, no. 10, 2006, pp. 747-60.
Trost BM, Machacek MR, Aponick A. Predicting the stereochemistry of diphenylphosphino benzoic acid (DPPBA)-based palladium-catalyzed asymmetric allylic alkylation reactions: a working model. Acc Chem Res. 2006;39(10):747-60.
Trost, B. M., Machacek, M. R., & Aponick, A. (2006). Predicting the stereochemistry of diphenylphosphino benzoic acid (DPPBA)-based palladium-catalyzed asymmetric allylic alkylation reactions: a working model. Accounts of Chemical Research, 39(10), 747-60.
Trost BM, Machacek MR, Aponick A. Predicting the Stereochemistry of Diphenylphosphino Benzoic Acid (DPPBA)-based Palladium-catalyzed Asymmetric Allylic Alkylation Reactions: a Working Model. Acc Chem Res. 2006;39(10):747-60. PubMed PMID: 17042475.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Predicting the stereochemistry of diphenylphosphino benzoic acid (DPPBA)-based palladium-catalyzed asymmetric allylic alkylation reactions: a working model. AU - Trost,Barry M, AU - Machacek,Michelle R, AU - Aponick,Aaron, PY - 2006/10/18/pubmed PY - 2007/7/19/medline PY - 2006/10/18/entrez SP - 747 EP - 60 JF - Accounts of chemical research JO - Acc Chem Res VL - 39 IS - 10 N2 - Palladium-catalyzed asymmetric allylic alkylation has proven to be a powerful method for the preparation of a wide variety of chiral compounds and the rapid assembly of complex molecular architecture from simple starting materials. While many types of catalyst systems have been successfully employed with certain systems, diphenylphosphino benzoic acid (DPPBA) based ligands have found use over a broad range of substrate classes. This Account highlights the mechanistic aspects considered when designing reactions with DPPBA-based ligands and presents a working model for the a priori prediction of their stereochemical outcome. SN - 0001-4842 UR - https://www.unboundmedicine.com/medline/citation/17042475/Predicting_the_stereochemistry_of_diphenylphosphino_benzoic_acid__DPPBA__based_palladium_catalyzed_asymmetric_allylic_alkylation_reactions:_a_working_model_ L2 - https://doi.org/10.1021/ar040063c DB - PRIME DP - Unbound Medicine ER -