Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 5, Pages 4296-4303Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c02862
Keywords
-
Categories
Funding
- National Science Foundation [OCI-1053575, CHE-1764328]
- Irish Research Council (IRC) [GOIPG/2014/343, GOIPG/2017/7]
- Science Foundation Ireland [09/RFP/CHS2353, SFI/12/IP/1315, SFI/12/RC/2275]
- Science Foundation Ireland (SFI) [09/RFP/CHS2353] Funding Source: Science Foundation Ireland (SFI)
- Irish Research Council (IRC) [GOIPG/2017/7, GOIPG/2014/343] Funding Source: Irish Research Council (IRC)
Ask authors/readers for more resources
Density functional theory computations have elucidated the mechanism and origins of stereoselectivity in McGlacken's aldol-Tishchenko reaction, with variations of stereochemical outcome dependent on the nature of the ketone starting materials used. The intramolecular hydride transfer step is the key rate- and stereochemistry-determining step in this process.
Density functional theory computations have elucidated the mechanism and origins of stereoselectivity in McGlacken's aldol-Tishchenko reaction for the diastereoselective synthesis of 1,3-amino alcohols using Ellman's t-butylsulfinimines as chiral auxiliaries. Variations of stereochemical outcome are dependent on the nature of the ketone starting materials used, and the aspects leading to these differences have been rationalized. The intramolecular hydride transfer step is the rate- and stereochemistry-determining step, and all prior steps are reversible.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available