✦ LIBER ✦
Effects of γ-hydroxyl groups in lithium-ammonia reductions of α,β-unsaturated carbonyl compounds via an inverse-addition, low-temperature method
✍ Scribed by Ae. de Groot; B. J. M. Jansen; A. G. J. M. Peterse; J. B. P. A. Wijnberg
- Publisher
- Elsevier Science
- Year
- 2010
- Tongue
- English
- Weight
- 468 KB
- Volume
- 101
- Category
- Article
- ISSN
- 0165-0513
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✦ Synopsis
Abstract
A new inverse‐addition, low‐temperature procedure for lithium‐ammonia reductions has been developed. Using this method it has been demonstrated that the reduction of ethyl 5,5‐(ethylenedioxy)‐8β‐hydroxy‐4aβ‐methyl‐2‐oxo‐2,3,4,4a,5,6,7,8‐octahydro‐1‐naphthalenecarboxylate (3) results in an unusual cis‐reduction product. The 8β‐hydroxyl group, low reaction temperature (–80°C) and addition of lithium‐ammonia to the substrate all proved to be necessary in order to achieve this cis reduction.