Double Asymmetric Dihydroxylation of 1,5-Hexadiene

✍ Scribed by Maier, Martin E. ;Reuter, Sebastian

• Book ID: 102366879
• Publisher: John Wiley and Sons
• Year: 1997
• Tongue: English
• Weight: 427 KB
• Volume: 1997
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.199719971006

✦ Synopsis

Abstract

Double asymmetric dihydroxylation of 1,5‐hexadiene gave in one step a mixture of the d,l/meso tetrols 6 in a ratio of 3.4:1. From this ratio a facial selectivity of 6.65:1 for each double bond can be calculated. As a consequence of the double reaction the d/l ratio can be estimated to be 44:1. Compound 6 served then as starting material for the preparation of the bis‐epoxide 12 and the 2,5‐dihydroxyhexane (13). While the separation of the diastereomers was not possible so far, this route for the preparation of 6, 12 and 13 might still be useful because it is very short and products derived from them might allow the crucial separation.