Mechanism of enantioselective protonation of an enolate in the presence of a chiral phenolic additive

Chirality

Volumn 11, Issue 10, 1999, Pages 787-789

  Eames, Jason ^a   Weerasooriya, Neluka ^a  

^a QUEEN MARY UNIVERSITY OF LONDON   (United Kingdom)

Author keywords

Asymmetric synthesis; Auxiliary; Chiral and chemoselective protonation; Enantioselective synthesis and resolution

Indexed keywords

CARBONYL DERIVATIVE; PHENOL DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; PRIORITY JOURNAL; PROTON TRANSPORT; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032758431     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1520-636X(1999)11:10<787::AID-CHIR8>3.0.CO;2-0     Document Type: Article

References (13)

1. Fehr C. Enantioselective Protonation of Enolates and Enols. Angew Chem Int Engl 1996;35:2566-2587.
2. Asensio G, Aleman P, Cuenca A, Gil J, Medio-Simon M. Efficient asymmetric protonation of enolates with readily accessible chiral alpha-sulfinyl alcohols. Tetrahedron: Asymmetry 1998;9:4073-4078.
3. Muzart J, Hénin F, Aboulhoda SA. Asymetric protonation of enolic species: dramatic increase in the selectivity with temperature and unexpected Eyring diagram. Tetrahedron: Asymmetry 1997;8:381-389.
4. Yasukata T, Koga K. Enantioselective protonation of Achira lithium enolates using a chiral amine in the presence of lithium bromide. Tetrahedron: Asymmetry 1993;4:35-38.
5. Bolm C, Weickhardt K, Zehnder M, Ranff T. Synthesis of optically active bis(2-oxazolines): crystal structure of a 1,2-bis(2-oxazolinyl)-benzene.ZnC12 complex. Chem Ber 1991;124:1173-1180.
6. Bolm C, Weickhardt K, Zehnder M, Glasmacher D. Syntheses and crystal structures of 4,5-dihydro-2-(2′-hydroxyphenyl)oxazole-containing metal compelexes. Helv Chim Acta 1991;74:717-726.
7. Krause N, Ebert S, Haubrich A Diastereoselective protonation of chiral enolates with chelatin proton donors under reagent control: scope, mechanism, and applications. Liebigs Ann/Recueil 1997;2409-2148 and references therein.
8. Duhamel L, Plaquevent J-C. Deracemisation by Enantioselective Protonation VI - An improvement method for Enantiomeric enrichment of alpha-amino acids using metalation by means of a Chiral amide. Tetrahedron Lett 1980;21:2521-2524.
9. Eames J. Diastereoselective Protonation of Chiral Enolates derived from 2,4-Dimethyl-1-tetralone using Carbonyl Chelating Proton Donors Tetrahedron Lett 1999;40:5787-5790.
10. Gerlach U, Hünig S. Enantioselective protonation of carbanions with chiral proton sources. Angew Chem Int Ed Engl Ed 1987;26:1283-1285.
11. Potin D, Williams K, Rebek J. Asymmetric protonation of enolates. Angew Chem Int Engl Ed 1990;29:1420-1421.
12. Eigen M. Proton Transfer, Acid-Base Catalysis and Enzymatic Hydrolysis. Angew Chem Int Engl 1964;3:1 and references therein.
13. Zimmerman HE. Kinetic protonation of enols, enolates, and analogues. The stereochemistry fo ketonization. Acc Chem Res 1987;20:263-268.