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Copper-catalyzed divergent kinetic resolution of racemic allylic substrates.
Chirality. 2011 Oct; 23(9):703-10.C

Abstract

When a racemic mixture is fully consumed the products may still be enantiomerically enriched. In particular, the regiodivergent kinetic resolution is a process in which a single chiral catalyst or reagent reacts with a racemic substrate to form regioisomers possessing an opposite configuration on the newly-formed stereogenic centers. This review reports the major advances in the field of the copper-catalyzed regiodivergent and stereodivergent kinetic resolution of allylic substrates with organometallic reagents. The chiral recognition matching phenomena found with particular allylic substrates with the absolute configuration of the chiral catalyst allows in some cases an excellent control of the regio- and stereoselectivity, sheding some light on the so-called "black-box" mechanism of a copper-catalyzed asymmetric allylic alkylation.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Pineschi M
Dipartimento di Scienze Farmaceutiche, Sede di Chimica Bioorganica e Biofarmacia, Università di Pisa, Via Bonanno 33, Pisa, Italy. pineschi@farm.unipi.it
Di Bussolo V
No affiliation info available
Crotti P
No affiliation info available

MeSH

AlkylationAllyl CompoundsCatalysisCopperEpoxy CompoundsKineticsMolecular StructureOrganometallic CompoundsStereoisomerism

Pub Type(s)

Journal Article
Review

Language

eng

PubMed ID

21837639

Citation

Pineschi, Mauro, et al. "Copper-catalyzed Divergent Kinetic Resolution of Racemic Allylic Substrates." Chirality, vol. 23, no. 9, 2011, pp. 703-10.
Pineschi M, Di Bussolo V, Crotti P. Copper-catalyzed divergent kinetic resolution of racemic allylic substrates. Chirality. 2011;23(9):703-10.
Pineschi, M., Di Bussolo, V., & Crotti, P. (2011). Copper-catalyzed divergent kinetic resolution of racemic allylic substrates. Chirality, 23(9), 703-10. https://doi.org/10.1002/chir.20980
Pineschi M, Di Bussolo V, Crotti P. Copper-catalyzed Divergent Kinetic Resolution of Racemic Allylic Substrates. Chirality. 2011;23(9):703-10. PubMed PMID: 21837639.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Copper-catalyzed divergent kinetic resolution of racemic allylic substrates. AU - Pineschi,Mauro, AU - Di Bussolo,Valeria, AU - Crotti,Paolo, Y1 - 2011/08/12/ PY - 2011/03/15/received PY - 2011/05/17/accepted PY - 2011/8/13/entrez PY - 2011/8/13/pubmed PY - 2012/3/3/medline SP - 703 EP - 10 JF - Chirality JO - Chirality VL - 23 IS - 9 N2 - When a racemic mixture is fully consumed the products may still be enantiomerically enriched. In particular, the regiodivergent kinetic resolution is a process in which a single chiral catalyst or reagent reacts with a racemic substrate to form regioisomers possessing an opposite configuration on the newly-formed stereogenic centers. This review reports the major advances in the field of the copper-catalyzed regiodivergent and stereodivergent kinetic resolution of allylic substrates with organometallic reagents. The chiral recognition matching phenomena found with particular allylic substrates with the absolute configuration of the chiral catalyst allows in some cases an excellent control of the regio- and stereoselectivity, sheding some light on the so-called "black-box" mechanism of a copper-catalyzed asymmetric allylic alkylation. SN - 1520-636X UR - https://www.unboundmedicine.com/medline/citation/21837639/Copper_catalyzed_divergent_kinetic_resolution_of_racemic_allylic_substrates_ L2 - https://doi.org/10.1002/chir.20980 DB - PRIME DP - Unbound Medicine ER -