Improved Synthesis of (±)-4,12-Dihydroxy[2.2]paracyclophane and Its Enantiomeric Resolution by Enzymatic Methods: Planar Chiral (R)- and (S)-Phanol
- 29 October 2002
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 67 (24) , 8679-8681
- https://doi.org/10.1021/jo020451x
Abstract
(±)-4,12-Dihydroxy[2.2]paracyclophane [(±)-PHANOL] is readily prepared from [2.2]paracyclophane by an improved synthetic protocol. Enzymatic kinetic resolution of its bis-acetate proceeds with good enantioselection. Separation, hydrolysis, and recrystallization provides both enantiomers of PHANOL in high enantiopurity.Keywords
This publication has 10 references indexed in Scilit:
- A potential ambiguity in the stereochemical description of complex paracyclophanesTetrahedron: Asymmetry, 1998
- Synthesis and Crystal Structure of Phosphorus(V) Nitride α‐P3N5Angewandte Chemie International Edition in English, 1997
- Kinetic Resolution of rac-4,12-Dibromo[2.2]paracyclophane in a Palladium [2.2]PHANEPHOS Catalyzed AminationThe Journal of Organic Chemistry, 1997
- Effects of torsional angles of 2,2′-biaryldiol ligands in asymmetric Diels-Alder reactions of acrylates catalyzed by their titanium complexesTetrahedron: Asymmetry, 1996
- Catalytic asymmetric Michael reactions promoted by the La-Na-BINOL complex (LSB). Enantioface selection on Michael donorsTetrahedron Letters, 1996
- Catalytic Asymmetric Michael Reactions Promoted by a Lithium-Free Lanthanum-BINOL ComplexJournal of the American Chemical Society, 1994
- Asymmetric ene reactions in organic synthesisChemical Reviews, 1992
- Chiral titanium complex-catalyzed Diels-Alder reaction: A practical route to anthracycline intermediatesTetrahedron: Asymmetry, 1991
- Book Review: Gaps and Verges. By R. HoffmannAngewandte Chemie International Edition in English, 1990
- Synthesis of 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (BINAP), an atropisomeric chiral bis(triaryl)phosphine, and its use in the rhodium(I)-catalyzed asymmetric hydrogenation of .alpha.-(acylamino)acrylic acidsJournal of the American Chemical Society, 1980