Facile Optical Resolution of tert‐Butanethiosulfinate by Molecular Complexation with (R)‐BINOL and Study of Chiral Discrimination of the Diastereomeric Complexes
Authors:
- 28 May 2003
- journal article
- research article
- Published by Wiley in Chemistry – A European Journal
- Vol. 9 (11) , 2611-2615
Abstract
An important synthon, tert‐butanethiosulfinate (2), has been effectively resolved by forming molecular complexes with (R)‐2,2′‐dihydroxy‐1,1′‐binaphthyl (BINOL, 3) in high enantioselectivity (>99 % ee). The present procedure represents the first example of the resolution of thiosulfinate. The mechanism of chiral discrimination is discussed in terms of molecular recognition based on IR and Xray analyses of the diastereomeric complexes during the resolution. In the less‐soluble complex, (R)‐3 and (R)‐2 self‐assembled as a linear supramolecule; however, in the more‐soluble complex, (R)‐3 and (S)‐2 formed a simple bimolecular complex by one stronger hydrogen bond. Hydrogen bonding is the major driving force for effective resolution.Keywords
This publication has 48 references indexed in Scilit:
- Enantioselective Inclusion of Methyl Phenyl Sulfoxides and Benzyl Methyl Sulfoxides by (R)-Phenylglycyl-(R)-phenylglycine and the Crystal Structures of the Inclusion CavitiesThe Journal of Organic Chemistry, 1999
- N-Nitrosopiperidines with chirality solely due to hindered rotation about the N–N bond: enantioselective inclusion complexation with optically active hostsChemical Communications, 1999
- Asymmetric Synthesis using Sulfinimines (Thiooxime S-Oxides)Phosphorus, Sulfur, and Silicon and the Related Elements, 1997
- Optical resolution of methyl phenyl and benzyl methyl sulfoxides and alkyl phenylsulfinates by complexation with chiral host compounds derived from tartaric acidJournal of the Chemical Society, Chemical Communications, 1995
- Optical Resolution of Binaphthyl and Biphenanthryl Diols by Inclusion Crystallization with N-Alkylcinchonidium Halides. Structural Characterization of the Resolved MaterialsThe Journal of Organic Chemistry, 1994
- Resolution of Racemates by Distillation with Inclusion CompoundsAngewandte Chemie International Edition, 1994
- Destillative Racematspaltung mit Hilfe von EinschlußverbindungenAngewandte Chemie, 1994
- Preparation of optically active 5-alkoxyfuran-2(5H)-ones and 5-methoxydihydrofuran-2(3H)-one by chiral inclusion complexationJournal of the Chemical Society, Chemical Communications, 1994
- Optical resolution of phosphinates and phosphine oxides by complex formation with optically active 2,2'-dihydroxy-1,1'-binaphthyl and crystallographic study of two diastereomeric complexes with methyl methylphenylphosphinateThe Journal of Organic Chemistry, 1988
- Induced asymmetric polymerisation of optically active vinyl sulphoxideJournal of the Chemical Society, Chemical Communications, 1986