Document Type
Article
Publication Date
8-15-2022
Publisher
Wiley
Source Publication
Angewandte Chemie International Edition
Source ISSN
1433-7851
Original Item ID
DOI: 10.1002/anie.202207275
Abstract
Fundamental to the synthesis of enantioenriched chiral molecules is the ability to assign absolute configuration at each stereogenic center, and to determine the enantiomeric excess for each compound. While determination of enantiomeric excess and absolute configuration is often considered routine in many facets of asymmetric synthesis, the same determinations for enantioisotopomers remains a formidable challenge. Here, we report the first highly enantioselective metal-catalyzed synthesis of enantioisotopomers that are chiral by virtue of deuterium substitution along with the first general spectroscopic technique for assignment of the absolute configuration and quantitative determination of the enantiomeric excess of isotopically chiral molecules. Chiral tag rotational spectroscopy uses noncovalent chiral derivatization, which eliminates the possibility of racemization during derivatization, to perform the chiral analysis without the need of reference samples oft he enantioisotopomer.
Recommended Citation
Mills, Mitchell D.; Sonstrom, Reilly E.; Vang, Zoua Pa; Neill, Justin L.; Scolati, Haley N.; West, Channing T.; Pate, Brooks H.; and Clark, Joseph R., "Enantioselective Synthesis of Enantioisotopomers with Quantitative Chiral Analysis by Chiral Tag Rotational Spectroscopy" (2022). Chemistry Faculty Research and Publications. 1070.
https://epublications.marquette.edu/chem_fac/1070
Comments
Accepted version. Angewandte Chemie International Edition, Vol. 61, No. 33 (August 15, 2022). DOI. © 2022 Wiley-VCH Verlag. Used with permission.