Journal article
A Silicon Tether Approach for Diastereocontrol in Radical Addition to Chiral Hydrazones
Organic letters, Vol.1(9), pp.1499-1501
11/04/1999
DOI: 10.1021/ol991059h
Abstract
A radical carbon−carbon bond construction approach to chiral α-branched amines is presented. Stereocontrolled radical addition to chiral hydrazones can be achieved by virtue of conformational constraints imposed during cyclizations using a temporary silicon connection. Oxidative removal of the tether completes the hydroxymethylation process to afford anti -2-hydrazino-1,3-diols in good yield. The 1,2-induction increases with increasing A values of the appended groups, consistent with prediction by the Beckwith−Houk model for stereocontrol in 5-hexenyl radical cyclizations.
Details
- Title: Subtitle
- A Silicon Tether Approach for Diastereocontrol in Radical Addition to Chiral Hydrazones
- Creators
- Gregory K Friestad
- Resource Type
- Journal article
- Publication Details
- Organic letters, Vol.1(9), pp.1499-1501
- Publisher
- American Chemical Society
- DOI
- 10.1021/ol991059h
- ISSN
- 1523-7060
- eISSN
- 1523-7052
- Language
- English
- Date published
- 11/04/1999
- Academic Unit
- Chemistry
- Record Identifier
- 9983985995502771
Metrics
9 Record Views