Published January 26, 2016
| Accepted Version + Supplemental Material
Journal Article
Open
Stereoelectronic Model To Explain Highly Stereoselective Reactions of Seven-Membered-Ring Oxocarbenium-Ion Intermediates
Abstract
Nucleophilic attack on seven-membered-ring oxocarbenium ions is generally highly stereoselective. The preferred mode of nucleophilic attack forms the product in a conformation that minimizes transannular interactions, thus leading to different stereoselectivity as compared to that of reactions involving six-membered-ring oxocarbenium ions.
Additional Information
© 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. Received: August 20, 2015; Revised: October 20, 2015; Published online: January 6, 2016. This research was supported by the National Institutes of Health, National Institute of General Medical Sciences (GM-61066). We thank Dr. Chin Lin (NYU) for assistance with NMR spectroscopy and mass spectrometry, and Dr. Chunhua Hu (NYU) for assistance with crystallographic studies.Attached Files
Accepted Version - nihms765618.pdf
Supplemental Material - anie201507806-sup-0001-misc_information.pdf
Files
anie201507806-sup-0001-misc_information.pdf
Files
(30.4 MB)
| Name | Size | Download all |
|---|---|---|
|
md5:7ff443e9b7796e5d014ae1c8104574b7
|
29.9 MB | Preview Download |
|
md5:8aa7b0d9856c0a24f96b99c1d6dc7448
|
499.2 kB | Preview Download |
Additional details
- Alternative title
- Stereoelectronic Model to Explain Highly Stereoselective Reactions of Seven-membered Ring Oxocarbenium Ion Intermediates
- PMCID
- PMC4811184
- Eprint ID
- 63927
- Resolver ID
- CaltechAUTHORS:20160125-105100347
- GM-61066
- NIH
- Created
-
2016-01-25Created from EPrint's datestamp field
- Updated
-
2022-05-13Created from EPrint's last_modified field