✦ LIBER ✦
Chiral [2H]-Labelled Methylene Groups in Trienoic- and Dienoic Fatty Acids: A Facile Approach via Asymmetric Epoxidation of [2H] Allyl Alcohols
✍ Scribed by Christoph Neumann; Wilhelm Boland
- Publisher
- John Wiley and Sons
- Year
- 1990
- Tongue
- German
- Weight
- 499 KB
- Volume
- 73
- Category
- Article
- ISSN
- 0018-019X
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✦ Synopsis
Abstract
Chiral [^2^H] ‐labelled methylene groups flanked by two double bonds within (poly)unsaturated fatty acids are readily available from trans‐2,3‐epoxy[2,3‐^2^H~2~] alk‐4‐yn‐l‐ols, obtained in their turn by asymmetric epoxidation of the corresponding (E)‐[2,3‐^2^H~2~] alk‐2‐en‐4‐yn‐l‐ols (see Scheme 3). The procedure is exemplified for (8S,3Z,6Z,9Z)‐[7,8‐^2^H~2~] trideca‐3,6,9‐trienoic acid ((8__S__)‐11) and (8__R__)‐11 (Scheme 4) as well as for (5__S__,3__Z__,6__Z__)‐[4,5^−2^H~2~]deca‐3,6‐dienoic acid ((5__S__)‐13) and (5__R__)‐13 (Scheme 5).