A highly stereoselective synthesis of s(-)-[1,1′-binaphthalene]-2,2′-diol
✍ Scribed by J. Brussee; A.C.A. Jansen
- Publisher
- Elsevier Science
- Year
- 1983
- Tongue
- French
- Weight
- 101 KB
- Volume
- 24
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
The title compound is synthesized from 2-naphthol by a S-(+)-amphetamine-copper (II) complex in high chemical yield (85%)_and high optical purity (up to 95%).
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## Abstract An economic and practical method for preparing enantiomerically pure [1,1′‐binaphthalene]‐2,2′‐diols is reported. Thus, a condensate of __threo__‐(1__S__,2__S__)‐2‐amino‐1‐(4‐nitrophenyl)propane‐1,3‐diol and cyclohexanone (CHANP) was used as a resolving agent. A 2 : 1 : 1 mixture of rac
The synthesis and resolution of 3,3%-bis(benzyloxy)-1,1%-binaphthalene-2,2%-diol 1 is described. A diastereomeric mixture of 7 (derived from (±)-1 and Boc-Ala-OH) was separated using crystallization and column chromatography.