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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 of the enantioisotopomer.
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Asymmetric Synthesis of P-Stereogenic Secondary Phosphine Oxides (SPOs)
Abstract P-Stereogenic secondary phosphine oxides [SPOs, RR′P(O)H], valuable ligands for metal complexes in asymmetric catalysis, are also building blocks for other chiral phosphorus derivatives. This short review summarizes methods used for asymmetric synthesis of P-stereogenic SPOs. 1 Introduction 2 Configurational Stability of P-Stereogenic SPOs 3 Classical Resolution, HPLC Separation, and Dynamic Resolution 4 Synthesis via Chiral Auxiliaries 5 Kinetic Resolution 6 Conclusions and Outlook
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- Award ID(s):
- 1954412
- PAR ID:
- 10331641
- Date Published:
- Journal Name:
- Synthesis
- Volume:
- 54
- Issue:
- 02
- ISSN:
- 0039-7881
- Page Range / eLocation ID:
- 271 to 280
- Format(s):
- Medium: X
- Sponsoring Org:
- National Science Foundation
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- Free Publicly Accessible Full Text
-
Accepted Manuscript1.0
- Journal Article:
- https://doi.org/10.1055/a-1582-0169
