Abstract
Enantioenriched secondary allylic carbamates have been deprotonated with sBuLi and reacted with boronic esters. In contrast to other electrophiles, high alpha-selectivity was observed and the boronate complexes were formed with almost complete retention of stereochemistry. The boronate complexes underwent a stereospecific 1,2-migration leading to tertiary allylic boronic esters with high er (>98:2). The scope of the reaction has been explored and found to embrace a broad range of both allylic carbamates and boronic esters. The methodology has been applied to an eight-step, stereoselective synthesis of each of the diastereoisomers of C30 botryococcene.
| Original language | English |
|---|---|
| Pages (from-to) | 7570-7574 |
| Number of pages | 5 |
| Journal | Journal of the American Chemical Society |
| Volume | 134 |
| Issue number | 17 |
| DOIs | |
| Publication status | Published - 2 May 2012 |
Research Groups and Themes
- Organic & Biological
Keywords
- METALATED NITROGEN DERIVATIVES
- HOMOALDOL REACTION
- ORGANIC-SYNTHESIS
- ENANTIOSELECTIVE SYNTHESIS
- ALKENE-1,1-DIBORONIC ESTERS
- TETRASUBSTITUTED OXIRANES
- STEREOSELECTIVE-SYNTHESIS
- STABILIZED CARBANIONS
- HOMOENOLATE REAGENTS
- ASYMMETRIC-SYNTHESIS
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