The 1,4-addition of the lithium enolate of methyldithioacetate (LMDTA) to (+/-)-4-O-TBS-2-cyclohexenone (3) can be varied from being highly 3,4-trans selective to being highly 3,4-cis selective simply by varying the reaction temperature. This stereodivergency allows expedient syntheses of the corresponding trans and cis methyl esters 6t and 6c and derived bicyclic ketolactones 7t and 7c.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/ol0611090 | DOI Listing |
Publication Analysis
Top Keywords
14-addition lithium
8
cis trans
4
trans selective
4
selective 14-addition
4
lithium dithioester
4
dithioester enolate
4
enolate 4-o-tbs-2-cyclohexenone
4
4-o-tbs-2-cyclohexenone 14-addition
4
lithium enolate
4
enolate methyldithioacetate
4
Similar Publications
Want AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!