In a series of important papers 192 Nguyen Trong Anh and collaborators have discussed the importance of charge control vs. orbital control3 in reaction of nucleophiles with ambident4 sub-strates. Hard nucleophiles5 react in charge-controlled fashion whereas orbital control tends to prevail for soft
Highly regioselective additions of certain 2-lithio-1,3-dithianes to conjugated ketones
โ Scribed by Paul C. Ostrowski; Vinayak V. Kane
- Publisher
- Elsevier Science
- Year
- 1977
- Tongue
- French
- Weight
- 226 KB
- Volume
- 18
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
โฆ Synopsis
Since the late 1960's, considerable effort has been devoted towards the discovery of useful synthetic equivalents of the acyl anion'.
Among the most widely used reagents are the metalated 1,3-dithiane derivatives2. The Michael addition of these acyl anion equivalents to a,B-unsaturated ketones is a reaction of particular synthetic utility, which has received significant attention and generally affords 1,2-addition products2. However, two recent publications have
๐ SIMILAR VOLUMES
The dithiane synthesis of carbonyl compounds, as developed by Corey and coworkers , involves the conversion of the potential carbonyl carbon into a reactive 2-lithio-1,3-dithiane. We have